NPASS Compound

Structure

CID158059 OpenBabel06191715532D 34 38 0 0 1 0 0 0 0 0999 V2000 -5.0629 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5058 -1.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0186 -0.6177 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.9487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8438 1.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 0.9744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8625 -0.8438 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6876 -0.9744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8438 -1.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2191 1.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6876 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6876 -2.9231 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8438 -2.4359 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8438 0.4872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3753 1.9487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8438 1.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6876 1.9487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2191 0.4872 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6876 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6876 -0.9744 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.9744 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5315 -2.4359 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5315 0.4872 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5315 2.4359 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5315 -1.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8438 -1.4615 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8438 0.4872 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3753 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5315 1.4615 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3753 -2.9231 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6876 2.9231 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3753 2.9231 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8881 -0.8438 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 1 0 0 0 0 2 25 1 0 0 0 0 3 25 1 0 0 0 0 5 27 1 0 0 0 0 8 9 1 0 0 0 0 8 19 2 0 0 0 0 9 21 1 0 0 0 0 10 15 1 0 0 0 0 10 18 1 0 0 0 0 11 14 1 0 0 0 0 11 20 1 0 0 0 0 12 13 1 0 0 0 0 12 22 1 0 0 0 0 13 26 1 0 0 0 0 14 28 1 0 0 0 0 15 30 1 0 0 0 0 16 17 1 0 0 0 0 16 27 1 0 0 0 0 17 30 1 0 0 0 0 18 29 1 6 0 0 0 19 23 1 0 0 0 0 19 27 1 0 0 0 0 20 25 1 0 0 0 0 20 26 1 1 0 0 0 21 26 1 1 0 0 0 21 28 1 0 0 0 0 22 25 1 0 0 0 0 22 31 1 1 0 0 0 23 29 1 6 0 0 0 23 30 1 0 0 0 0 24 32 2 0 0 0 0 24 33 1 0 0 0 0 26 4 1 1 0 0 0 27 28 1 1 0 0 0 28 6 1 1 0 0 0 29 7 1 1 0 0 0 29 34 1 0 0 0 0 30 24 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	472.36
Volume:	514.542
LogP:	5.258
LogD:	4.712
LogS:	-4.271
# Rotatable Bonds:	1
TPSA:	77.76
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.397
Synthetic Accessibility Score:	4.864
Fsp3:	0.9
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.422
MDCK Permeability:	1.660302405070979e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.104
30% Bioavailability (F30%):	0.89

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.33
Plasma Protein Binding (PPB):	94.35298919677734%
Volume Distribution (VD):	0.657
Pgp-substrate:	4.080790042877197%

ADMET: Metabolism

CYP1A2-inhibitor:	0.009
CYP1A2-substrate:	0.44
CYP2C19-inhibitor:	0.012
CYP2C19-substrate:	0.849
CYP2C9-inhibitor:	0.148
CYP2C9-substrate:	0.466
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.15
CYP3A4-inhibitor:	0.253
CYP3A4-substrate:	0.201

ADMET: Excretion

Clearance (CL):	2.664
Half-life (T1/2):	0.132

ADMET: Toxicity

hERG Blockers:	0.004
Human Hepatotoxicity (H-HT):	0.203
Drug-inuced Liver Injury (DILI):	0.012
AMES Toxicity:	0.002
Rat Oral Acute Toxicity:	0.855
Maximum Recommended Daily Dose:	0.968
Skin Sensitization:	0.259
Carcinogencity:	0.044
Eye Corrosion:	0.66
Eye Irritation:	0.429
Respiratory Toxicity:	0.986

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC158059

Natural Product ID:	NPC158059
*Common Name:**	Pomolic Acid
IUPAC Name:	(1R,2R,4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-1,10-dihydroxy-1,2,6a,6b,9,9,12a-heptamethyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
Synonyms:	Pomolic Acid
Standard InCHIKey:	ZZTYPLSBNNGEIS-OPAXANQDSA-N
Standard InCHI:	InChI=1S/C30H48O4/c1-18-10-15-30(24(32)33)17-16-27(5)19(23(30)29(18,7)34)8-9-21-26(4)13-12-22(31)25(2,3)20(26)11-14-28(21,27)6/h8,18,20-23,31,34H,9-17H2,1-7H3,(H,32,33)/t18-,20+,21-,22+,23-,26+,27-,28-,29-,30+/m1/s1
SMILES:	O[C@H]1CC[C@]2([C@H](C1(C)C)CC[C@@]1([C@@H]2CC=C2[C@@]1(C)CC[C@@]1([C@H]2[C@](C)(O)[C@H](C)CC1)C(=O)O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL486986
PubChem CID:	382831
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO28011	Swertia japonica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1007/BF02675902]
NPO11144	Centella asiatica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1007/s11816-015-0350-y]
NPO3595	Euscaphis japonica	Species	Staphyleaceae	Eukaryota	n.a.	twig	n.a.	DOI[10.1021/np1003593]
NPO28011	Swertia japonica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1055/s-2008-1074888]
NPO28011	Swertia japonica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1248/cpb.30.4088]
NPO28011	Swertia japonica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10353265]
NPO20081	Mycobacterium tuberculosis	Species	Mycobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[10553679]
NPO22175	Perovskia abrotanoides	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11720520]
NPO20081	Mycobacterium tuberculosis	Species	Mycobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[12055308]
NPO9096	Scutellaria lateriflora	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12713409]
NPO20081	Mycobacterium tuberculosis	Species	Mycobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[15070765]
NPO28035	Streptomyces fumanus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[15730262]
NPO13968	Garcinia scortechinii	Species	Clusiaceae	Eukaryota	fruits	n.a.	n.a.	PMID[16038540]
NPO14358	Rhodobacter sphaeroides	Species	Rhodobacteraceae	Bacteria	n.a.	n.a.	n.a.	PMID[1612412]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[16309325]
NPO28391	Euonymus nanoides	Species	Celastraceae	Eukaryota	n.a.	seed	n.a.	PMID[16462067]
NPO22364	Weigela subsessilis	Species	Caprifoliaceae	Eukaryota	n.a.	leaf	n.a.	PMID[16595930]
NPO22364	Weigela subsessilis	Species	Caprifoliaceae	Eukaryota	n.a.	stem	n.a.	PMID[16595930]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	n.a.	Seoul, Korea	2000-Jun	PMID[16643034]
NPO11144	Centella asiatica	Species	Apiaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[17520525]
NPO5158	Cecropia pachystachya	Species	Urticaceae	Eukaryota	n.a.	leaf	n.a.	PMID[18260049]
NPO28528	Bridelia ferruginea	Species	Phyllanthaceae	Eukaryota	roots	Gabon	1987	PMID[18327911]
NPO28528	Bridelia ferruginea	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18327911]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	fruit	n.a.	n.a.	PMID[18505286]
NPO8068	Blumea mollis	Species	Asteraceae	Eukaryota	n.a.	leaf	n.a.	PMID[18566831]
NPO29554	Diospyros kaki	Species	Ebenaceae	Eukaryota	leaves	n.a.	n.a.	PMID[18798681]
NPO14162	Chlorophytum borivilianum	Species	Asparagaceae	Eukaryota	roots	n.a.	n.a.	PMID[19128156]
NPO20081	Mycobacterium tuberculosis	Species	Mycobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[19276083]
NPO9096	Scutellaria lateriflora	Species	Lamiaceae	Eukaryota	aerial parts	n.a.	n.a.	PMID[19555121]
NPO9096	Scutellaria lateriflora	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19555121]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	fruit	n.a.	n.a.	PMID[19650637]
NPO7016	Gardenia tubifera	Species	Rubiaceae	Eukaryota	exudate	n.a.	n.a.	PMID[20028108]
NPO20081	Mycobacterium tuberculosis	Species	Mycobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[20448045]
NPO10946	Pseudallescheria boydii	Species	Microascaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20509707]
NPO28217	Septoria pistaciarum	Species	Mycosphaerellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20550123]
NPO12357	Lycopus europaeus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20674349]
NPO20081	Mycobacterium tuberculosis	Species	Mycobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[20843794]
NPO3595	Euscaphis japonica	Species	Staphyleaceae	Eukaryota	Twigs	Yangming mountain, Taiwan	2008-APR	PMID[20873721]
NPO11492	Kopsia grandifolia	Species	Apocynaceae	Eukaryota	n.a.	stem	n.a.	PMID[21428274]
NPO11492	Kopsia grandifolia	Species	Apocynaceae	Eukaryota	n.a.	leaf	n.a.	PMID[21428274]
NPO20081	Mycobacterium tuberculosis	Species	Mycobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[22194604]
NPO8650	Perilla frutescens	Species	Lamiaceae	Eukaryota	leaves	n.a.	n.a.	PMID[22272932]
NPO28217	Septoria pistaciarum	Species	Mycosphaerellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22530813]
NPO11144	Centella asiatica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22966846]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	fruits	n.a.	n.a.	PMID[23305920]
NPO10946	Pseudallescheria boydii	Species	Microascaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23964677]
NPO20081	Mycobacterium tuberculosis	Species	Mycobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[24516143]
NPO20081	Mycobacterium tuberculosis	Species	Mycobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[25028392]
NPO8650	Perilla frutescens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25320841]
NPO9096	Scutellaria lateriflora	Species	Lamiaceae	Eukaryota	aerial part	n.a.	n.a.	PMID[25442304]
NPO1795	Fragaria vesca	Species	Rosaceae	Eukaryota	n.a.	fruit	n.a.	PMID[26169681]
NPO20081	Mycobacterium tuberculosis	Species	Mycobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[26466957]
NPO20081	Mycobacterium tuberculosis	Species	Mycobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[26774486]
NPO28528	Bridelia ferruginea	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26938998]
NPO28011	Swertia japonica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26996316]
NPO20081	Mycobacterium tuberculosis	Species	Mycobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[27242221]
NPO20081	Mycobacterium tuberculosis	Species	Mycobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[27807341]
NPO13017	Nauclea latifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31429278]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32141747]
NPO29554	Diospyros kaki	Species	Ebenaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[3430165]
NPO3595	Euscaphis japonica	Species	Staphyleaceae	Eukaryota	n.a.	pericarp	n.a.	PMID[4421158]
NPO28011	Swertia japonica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[5583807]
NPO20081	Mycobacterium tuberculosis	Species	Mycobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[8917504]
NPO20081	Mycobacterium tuberculosis	Species	Mycobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[97292]
NPO16124	Hyptis capitata	Species	Lamiaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[9748372]
NPO9467	Rosa woodsii	Species	Rosaceae	Eukaryota	n.a.	leaf	n.a.	PMID[9748372]
NPO29554	Diospyros kaki	Species	Ebenaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO28011	Swertia japonica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28576	Berberis julianae	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3595	Euscaphis japonica	Species	Staphyleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13014	Ipomoea cairica	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8650	Perilla frutescens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12357	Lycopus europaeus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28696	Rhaponticum uniflorum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28334	Pyrola decorata	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13524	Pyrola japonica	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1795	Fragaria vesca	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11144	Centella asiatica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11144	Centella asiatica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[MetaboLights]
NPO4004	Aquilegia ecalcarata	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13968	Garcinia scortechinii	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12450	Cneorum pulverulentum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11144	Centella asiatica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16765	Knoxia valerianoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8650	Perilla frutescens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28576	Berberis julianae	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3595	Euscaphis japonica	Species	Staphyleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28011	Swertia japonica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28334	Pyrola decorata	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16703	Isodon lophanthoides	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1795	Fragaria vesca	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13524	Pyrola japonica	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12357	Lycopus europaeus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3465	Aconitum leucostomum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28696	Rhaponticum uniflorum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13014	Ipomoea cairica	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8650	Perilla frutescens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11144	Centella asiatica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO13014	Ipomoea cairica	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO13524	Pyrola japonica	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28011	Swertia japonica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28334	Pyrola decorata	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28696	Rhaponticum uniflorum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3465	Aconitum leucostomum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28576	Berberis julianae	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22699	Echinops setifer	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28011	Swertia japonica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO13524	Pyrola japonica	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO4163	Echinopsis latifolius	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11144	Centella asiatica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO16765	Knoxia valerianoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO8650	Perilla frutescens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28696	Rhaponticum uniflorum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28053	Quercus serrata	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12357	Lycopus europaeus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28161	Stephania sutchuenensis	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27990	Schizonepeta multifida	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28696	Rhaponticum uniflorum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16703	Isodon lophanthoides	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20081	Mycobacterium tuberculosis	Species	Mycobacteriaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO29353	Benzoin praecox	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO28633	Bystropogon origanifolius	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28691	Streptomyces odorifer	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO16124	Hyptis capitata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7016	Gardenia tubifera	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28670	Mortierella elongata	Species	Mortierellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28528	Bridelia ferruginea	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27867	Turbo argyrostoma	Species	Turbinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22175	Perovskia abrotanoides	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO205	Lasianthus fordii	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28334	Pyrola decorata	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10550	Artemisia hanseniana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8892	Sordaria araneosa	Species	Sordariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3595	Euscaphis japonica	Species	Staphyleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27943	Cardamine pinnata	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22364	Weigela subsessilis	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25704	Tetraneuris acaulis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28391	Euonymus nanoides	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3465	Aconitum leucostomum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14358	Rhodobacter sphaeroides	Species	Rhodobacteraceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO29115	Rhinella arenarum	Species	Bufonidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8068	Blumea mollis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28374	Pleogyne cunninghami	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13467	Anarsia lineatella	Species	Gelechiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28656	Lactobacillus casei	Species	Lactobacillaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO9467	Rosa woodsii	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4004	Aquilegia ecalcarata	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11144	Centella asiatica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28481	Cerbera dilatata	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27959	Codonocarpus australis	Species	Gyrostemonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28303	Pleogyne cunninghamii	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28269	Rubus rosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28073	Crateva nurvala	Species	Capparaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14162	Chlorophytum borivilianum	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3287	Hymenoxys scaposa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10946	Pseudallescheria boydii	Species	Microascaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5158	Cecropia pachystachya	Species	Urticaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28035	Streptomyces fumanus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO28200	Unonopsis glaucopetala	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12509	Dipterocarpus dyeri	Species	Dipterocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11441	Barbacenia flava	Species	Velloziaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13524	Pyrola japonica	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5191	Penicillium cinerascens	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1795	Fragaria vesca	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13968	Garcinia scortechinii	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28614	Zieria smithii	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8650	Perilla frutescens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26254	Fagus crenata	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28217	Septoria pistaciarum	Species	Mycosphaerellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13014	Ipomoea cairica	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16765	Knoxia valerianoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9096	Scutellaria lateriflora	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28596	Streptomyces lavendofoliae	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO25776	Buddleja scordioides	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16669	Diospyros verrucosa	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6331	Jacobaea subalpina	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13766	Ceanothus velutinus	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26412	Streptomyces tauricus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO4671	Persea mexicana	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28704	Agaricus hortensis	Species	Agaricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12450	Cneorum pulverulentum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11998	Ledebouria socialis	Species	Hyacinthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28509	Achillea clypeolata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28576	Berberis julianae	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO746	Panax innovans	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11492	Kopsia grandifolia	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28131	Polygala amara	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20395	Athanasia crithmifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13017	Nauclea latifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28011	Swertia japonica	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14057	Apollonias barbujana	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
EC50	3
GI50	53
IC50	8
MIC	1
Others	12

Activity Type	# Activity
Cell Line	63
CELL-LINE	3
Individual Protein	1
Organism	6
Others	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT759	Cell Line	H9	Homo sapiens	EC50	=	1.4	ug.mL-1	PMID[572543]
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	IC50	=	3900.0	nM	PMID[572544]
NPT759	Cell Line	H9	Homo sapiens	EC50	=	3000.0	nM	PMID[572542]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	17220.0	nM	PMID[572546]
NPT146	Cell Line	SK-OV-3	Homo sapiens	IC50	=	13950.0	nM	PMID[572546]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	IC50	=	19160.0	nM	PMID[572546]
NPT148	Cell Line	HCT-15	Homo sapiens	IC50	=	13720.0	nM	PMID[572546]
NPT83	Cell Line	MCF7	Homo sapiens	Activity	=	79.0	%	PMID[572547]
NPT397	Cell Line	NCI-H460	Homo sapiens	Activity	=	82.0	%	PMID[572547]
NPT139	Cell Line	HT-29	Homo sapiens	Activity	=	91.0	%	PMID[572547]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	Activity	=	92.0	%	PMID[572547]
NPT367	Cell Line	MDA-N	Homo sapiens	GI50	n.a.	16330.52	nM	PMID[572548]
NPT368	Cell Line	SN12C	Homo sapiens	GI50	n.a.	13645.83	nM	PMID[572548]
NPT370	Cell Line	NCI-H23	Homo sapiens	GI50	n.a.	18706.82	nM	PMID[572548]
NPT369	Cell Line	ACHN	Homo sapiens	GI50	n.a.	16519.62	nM	PMID[572548]
NPT371	Cell Line	UO-31	Homo sapiens	GI50	n.a.	11297.96	nM	PMID[572548]
NPT372	Cell Line	HOP-92	Homo sapiens	GI50	n.a.	4446.31	nM	PMID[572548]
NPT116	Cell Line	HL-60	Homo sapiens	GI50	n.a.	4345.1	nM	PMID[572548]
NPT90	Cell Line	DU-145	Homo sapiens	GI50	n.a.	8974.29	nM	PMID[572548]
NPT374	Cell Line	SF-539	Homo sapiens	GI50	n.a.	3250.87	nM	PMID[572548]
NPT375	Cell Line	Malme-3M	Homo sapiens	GI50	n.a.	12331.05	nM	PMID[572548]
NPT376	Cell Line	A498	Homo sapiens	GI50	n.a.	18967.06	nM	PMID[572548]
NPT111	Cell Line	K562	Homo sapiens	GI50	n.a.	6486.34	nM	PMID[572548]
NPT377	Cell Line	OVCAR-3	Homo sapiens	GI50	n.a.	18578.04	nM	PMID[572548]
NPT112	Cell Line	MOLT-4	Homo sapiens	GI50	n.a.	4864.07	nM	PMID[572548]
NPT378	Cell Line	NCI/ADR-RES	Homo sapiens	GI50	n.a.	15488.17	nM	PMID[572548]
NPT380	Cell Line	U-251	Homo sapiens	GI50	n.a.	14125.38	nM	PMID[572548]
NPT382	Cell Line	OVCAR-5	Homo sapiens	GI50	n.a.	17701.09	nM	PMID[572548]
NPT381	Cell Line	OVCAR-8	Homo sapiens	GI50	n.a.	20183.66	nM	PMID[572548]
NPT383	Cell Line	SNB-19	Homo sapiens	GI50	n.a.	15667.51	nM	PMID[572548]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	GI50	n.a.	8790.23	nM	PMID[572548]
NPT384	Cell Line	TK-10	Homo sapiens	GI50	n.a.	14454.4	nM	PMID[572548]
NPT385	Cell Line	SR	Homo sapiens	GI50	n.a.	13867.56	nM	PMID[572548]
NPT323	Cell Line	SW-620	Homo sapiens	GI50	n.a.	21928.05	nM	PMID[572548]
NPT455	Cell Line	NCI-H522	Homo sapiens	GI50	n.a.	13867.56	nM	PMID[572548]
NPT386	Cell Line	KM12	Homo sapiens	GI50	n.a.	12416.52	nM	PMID[572548]
NPT387	Cell Line	M14	Homo sapiens	GI50	n.a.	2978.52	nM	PMID[572548]
NPT389	Cell Line	RPMI-8226	Homo sapiens	GI50	n.a.	16255.49	nM	PMID[572548]
NPT456	Cell Line	OVCAR-4	Homo sapiens	GI50	n.a.	16826.74	nM	PMID[572548]
NPT390	Cell Line	LOX IMVI	Homo sapiens	GI50	n.a.	15739.83	nM	PMID[572548]
NPT457	Cell Line	BT-549	Homo sapiens	GI50	n.a.	14387.99	nM	PMID[572548]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	GI50	n.a.	17100.15	nM	PMID[572548]
NPT81	Cell Line	A549	Homo sapiens	GI50	n.a.	17218.69	nM	PMID[572548]
NPT391	Cell Line	HCC 2998	Homo sapiens	GI50	n.a.	14996.85	nM	PMID[572548]
NPT392	Cell Line	SNB-75	Homo sapiens	GI50	n.a.	13489.63	nM	PMID[572548]
NPT148	Cell Line	HCT-15	Homo sapiens	GI50	n.a.	10616.96	nM	PMID[572548]
NPT393	Cell Line	HCT-116	Homo sapiens	GI50	n.a.	12246.16	nM	PMID[572548]
NPT395	Cell Line	SF-268	Homo sapiens	GI50	n.a.	17139.57	nM	PMID[572548]
NPT394	Cell Line	EKVX	Homo sapiens	GI50	n.a.	18323.14	nM	PMID[572548]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	n.a.	19952.62	nM	PMID[572548]
NPT146	Cell Line	SK-OV-3	Homo sapiens	GI50	n.a.	17947.34	nM	PMID[572548]
NPT396	Cell Line	T47D	Homo sapiens	GI50	n.a.	16368.17	nM	PMID[572548]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	n.a.	5407.54	nM	PMID[572548]
NPT398	Cell Line	UACC-62	Homo sapiens	GI50	n.a.	3491.4	nM	PMID[572548]
NPT308	Cell Line	CAKI-1	Homo sapiens	GI50	n.a.	13963.68	nM	PMID[572548]
NPT400	Cell Line	MDA-MB-435	Homo sapiens	GI50	n.a.	15452.54	nM	PMID[572548]
NPT458	Cell Line	IGROV-1	Homo sapiens	GI50	n.a.	16519.62	nM	PMID[572548]
NPT399	Cell Line	SF-295	Homo sapiens	GI50	n.a.	3221.07	nM	PMID[572548]
NPT401	Cell Line	786-0	Homo sapiens	GI50	n.a.	5382.7	nM	PMID[572548]
NPT402	Cell Line	Hs-578T	Homo sapiens	GI50	n.a.	3515.6	nM	PMID[572548]
NPT403	Cell Line	UACC-257	Homo sapiens	GI50	n.a.	5420.01	nM	PMID[572548]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	GI50	n.a.	10256.52	nM	PMID[572548]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	GI50	n.a.	13614.45	nM	PMID[572548]
NPT407	Cell Line	COLO 205	Homo sapiens	GI50	n.a.	16443.72	nM	PMID[572548]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	IC50	=	48900.0	nM	PMID[572542]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	IC50	=	23.3	ug.mL-1	PMID[572543]
NPT27	Others	Unspecified		Ratio IC50/EC50	=	16.6	n.a.	PMID[572543]
NPT27	Others	Unspecified		Ratio IC50/EC50	=	16.3	n.a.	PMID[572542]
NPT27	Others	Unspecified		Activity	=	93.0	%	PMID[572547]
NPT20950	CELL-LINE	Erythrocyte	n.a.	Activity	=	0.101	mg/ml	PMID[572549]
NPT20950	CELL-LINE	Erythrocyte	n.a.	Activity	=	0.157	mg/ml	PMID[572549]
NPT450	Organism	Meloidogyne incognita	Meloidogyne incognita	EC	=	2.11	mM	PMID[572550]
NPT2	Others	Unspecified		IC50	=	9300.0	nM	PMID[572551]
NPT1122	Organism	Haemophilus influenzae	Haemophilus influenzae	MIC	=	18.8	ug.mL-1	PMID[572552]
NPT1122	Organism	Haemophilus influenzae	Haemophilus influenzae	MBC	=	50.0	ug ml-1	PMID[572552]
NPT1122	Organism	Haemophilus influenzae	Haemophilus influenzae	Ratio	=	2.7	n.a.	PMID[572552]
NPT27675	CELL-LINE	NRK-52E	Rattus norvegicus	EC50	=	14.2	nM	PMID[572553]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC158059 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	215
0.1-0.2	1361
0.2-0.3	4766
0.3-0.4	13533
0.4-0.5	9163
0.5-0.6	5802
0.6-0.7	4920
0.7-0.8	2356
0.8-0.85	243
0.85-0.9	131
0.9-0.95	147
0.95-1	60

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC202728
1.0	High Similarity	NPC118519
0.9885	High Similarity	NPC114159
0.9885	High Similarity	NPC6818
0.9885	High Similarity	NPC191412
0.9884	High Similarity	NPC187722
0.977	High Similarity	NPC229281
0.9767	High Similarity	NPC7260
0.9767	High Similarity	NPC477872
0.9767	High Similarity	NPC273621
0.9767	High Similarity	NPC120968
0.9767	High Similarity	NPC227467
0.9767	High Similarity	NPC290614
0.9767	High Similarity	NPC18872
0.9767	High Similarity	NPC210037
0.9663	High Similarity	NPC158371
0.9663	High Similarity	NPC132824
0.9663	High Similarity	NPC116457
0.9663	High Similarity	NPC207922
0.9663	High Similarity	NPC327179
0.9663	High Similarity	NPC62516
0.9663	High Similarity	NPC259733
0.9663	High Similarity	NPC157113
0.9655	High Similarity	NPC105189
0.9655	High Similarity	NPC38754
0.9651	High Similarity	NPC64872
0.9651	High Similarity	NPC198664
0.9651	High Similarity	NPC25906
0.9651	High Similarity	NPC143232
0.9651	High Similarity	NPC290972
0.9651	High Similarity	NPC274330
0.9556	High Similarity	NPC255589
0.9556	High Similarity	NPC187933
0.9556	High Similarity	NPC259788
0.9556	High Similarity	NPC247139
0.9556	High Similarity	NPC9613
0.9551	High Similarity	NPC96916
0.9545	High Similarity	NPC118490
0.954	High Similarity	NPC126369
0.954	High Similarity	NPC111110
0.954	High Similarity	NPC130278
0.954	High Similarity	NPC193750
0.954	High Similarity	NPC291028
0.954	High Similarity	NPC470589
0.9535	High Similarity	NPC473242
0.9535	High Similarity	NPC17733
0.9535	High Similarity	NPC470629
0.9535	High Similarity	NPC290690
0.9535	High Similarity	NPC182797
0.9535	High Similarity	NPC474512
0.9535	High Similarity	NPC52169
0.9535	High Similarity	NPC181225
0.9451	High Similarity	NPC174663
0.9444	High Similarity	NPC173744
0.9444	High Similarity	NPC73004
0.9444	High Similarity	NPC204961
0.9438	High Similarity	NPC148964
0.9438	High Similarity	NPC60692
0.9425	High Similarity	NPC127689
0.9425	High Similarity	NPC293048
0.9425	High Similarity	NPC130520
0.9425	High Similarity	NPC234346
0.9425	High Similarity	NPC121798
0.9425	High Similarity	NPC61543
0.9425	High Similarity	NPC263393
0.9425	High Similarity	NPC270768
0.9425	High Similarity	NPC470588
0.9425	High Similarity	NPC225585
0.9425	High Similarity	NPC59263
0.9419	High Similarity	NPC68160
0.9419	High Similarity	NPC242468
0.9419	High Similarity	NPC51700
0.9419	High Similarity	NPC88716
0.9419	High Similarity	NPC18064
0.9419	High Similarity	NPC307426
0.9419	High Similarity	NPC98442
0.9419	High Similarity	NPC102683
0.9419	High Similarity	NPC130577
0.9419	High Similarity	NPC171203
0.9419	High Similarity	NPC293564
0.9419	High Similarity	NPC142415
0.9348	High Similarity	NPC35239
0.9341	High Similarity	NPC43686
0.9333	High Similarity	NPC83693
0.9333	High Similarity	NPC473240
0.9333	High Similarity	NPC290481
0.9326	High Similarity	NPC275809
0.9318	High Similarity	NPC474728
0.931	High Similarity	NPC246708
0.931	High Similarity	NPC40552
0.9302	High Similarity	NPC72638
0.9247	High Similarity	NPC233012
0.9247	High Similarity	NPC118964
0.9247	High Similarity	NPC256247
0.9247	High Similarity	NPC54909
0.9239	High Similarity	NPC29765
0.9239	High Similarity	NPC271614
0.9239	High Similarity	NPC111214
0.9231	High Similarity	NPC476327
0.9231	High Similarity	NPC476318
0.9222	High Similarity	NPC159365
0.9222	High Similarity	NPC263548
0.9222	High Similarity	NPC209868
0.9222	High Similarity	NPC32407
0.9222	High Similarity	NPC299996
0.9222	High Similarity	NPC20235
0.9222	High Similarity	NPC231063
0.9222	High Similarity	NPC145667
0.9222	High Similarity	NPC88116
0.9222	High Similarity	NPC282395
0.9213	High Similarity	NPC235884
0.9213	High Similarity	NPC324341
0.9213	High Similarity	NPC306541
0.9213	High Similarity	NPC60755
0.9213	High Similarity	NPC71074
0.9213	High Similarity	NPC155120
0.9213	High Similarity	NPC84319
0.9213	High Similarity	NPC966
0.9213	High Similarity	NPC52021
0.9213	High Similarity	NPC145067
0.9213	High Similarity	NPC472149
0.9213	High Similarity	NPC25299
0.9213	High Similarity	NPC233455
0.9213	High Similarity	NPC282616
0.9213	High Similarity	NPC288833
0.9213	High Similarity	NPC300351
0.9213	High Similarity	NPC77099
0.9213	High Similarity	NPC158030
0.9213	High Similarity	NPC228784
0.9213	High Similarity	NPC285184
0.9213	High Similarity	NPC235704
0.9213	High Similarity	NPC4036
0.9213	High Similarity	NPC65120
0.9213	High Similarity	NPC474525
0.9213	High Similarity	NPC470590
0.9205	High Similarity	NPC474686
0.9205	High Similarity	NPC95246
0.9205	High Similarity	NPC474972
0.9205	High Similarity	NPC161751
0.9195	High Similarity	NPC71507
0.9195	High Similarity	NPC73064
0.913	High Similarity	NPC312075
0.913	High Similarity	NPC106112
0.913	High Similarity	NPC261935
0.913	High Similarity	NPC189880
0.913	High Similarity	NPC203343
0.9121	High Similarity	NPC32118
0.9121	High Similarity	NPC139570
0.9111	High Similarity	NPC133579
0.9111	High Similarity	NPC307335
0.9111	High Similarity	NPC298554
0.9111	High Similarity	NPC214756
0.9111	High Similarity	NPC136313
0.9111	High Similarity	NPC272075
0.9111	High Similarity	NPC63118
0.9111	High Similarity	NPC474806
0.9111	High Similarity	NPC295643
0.9111	High Similarity	NPC86368
0.9111	High Similarity	NPC49776
0.9111	High Similarity	NPC74855
0.9111	High Similarity	NPC474436
0.9101	High Similarity	NPC49320
0.9101	High Similarity	NPC120840
0.9101	High Similarity	NPC113989
0.9101	High Similarity	NPC46441
0.9101	High Similarity	NPC86372
0.9101	High Similarity	NPC172361
0.908	High Similarity	NPC74363
0.908	High Similarity	NPC73038
0.908	High Similarity	NPC475862
0.9032	High Similarity	NPC58942
0.9032	High Similarity	NPC260149
0.9032	High Similarity	NPC164349
0.9022	High Similarity	NPC201657
0.9022	High Similarity	NPC305464
0.9022	High Similarity	NPC307282
0.9022	High Similarity	NPC19376
0.9022	High Similarity	NPC25848
0.9011	High Similarity	NPC222047
0.9011	High Similarity	NPC91010
0.9011	High Similarity	NPC80365
0.9011	High Similarity	NPC87095
0.9011	High Similarity	NPC474529
0.9	High Similarity	NPC471588
0.9	High Similarity	NPC301244
0.9	High Similarity	NPC475708
0.9	High Similarity	NPC6255
0.8989	High Similarity	NPC30522
0.8977	High Similarity	NPC477926
0.8966	High Similarity	NPC133954
0.8958	High Similarity	NPC284865
0.8913	High Similarity	NPC474727
0.8913	High Similarity	NPC148523
0.8913	High Similarity	NPC53565
0.8913	High Similarity	NPC195715
0.8913	High Similarity	NPC198245
0.8876	High Similarity	NPC474511
0.8876	High Similarity	NPC1753
0.8864	High Similarity	NPC477579
0.8864	High Similarity	NPC56588

Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC158059 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	190
0.1-0.2	1687
0.2-0.3	3797
0.3-0.4	2279
0.4-0.5	733
0.5-0.6	208
0.6-0.7	181
0.7-0.8	67
0.8-0.85	4
0.85-0.9	3
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9213	High Similarity	NPD7515	Phase 2
0.8925	High Similarity	NPD7902	Approved
0.8804	High Similarity	NPD7748	Approved
0.8602	High Similarity	NPD7900	Approved
0.8602	High Similarity	NPD7901	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.8298	Intermediate Similarity	NPD6399	Phase 3
0.8191	Intermediate Similarity	NPD8034	Phase 2
0.8191	Intermediate Similarity	NPD8035	Phase 2
0.8068	Intermediate Similarity	NPD7645	Phase 2
0.8043	Intermediate Similarity	NPD3618	Phase 1
0.8022	Intermediate Similarity	NPD4786	Approved
0.8	Intermediate Similarity	NPD3667	Approved
0.7789	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7789	Intermediate Similarity	NPD5328	Approved
0.7778	Intermediate Similarity	NPD7525	Registered
0.7767	Intermediate Similarity	NPD5739	Approved
0.7767	Intermediate Similarity	NPD6675	Approved
0.7767	Intermediate Similarity	NPD6402	Approved
0.7767	Intermediate Similarity	NPD7128	Approved
0.7732	Intermediate Similarity	NPD4202	Approved
0.7714	Intermediate Similarity	NPD6372	Approved
0.7714	Intermediate Similarity	NPD6373	Approved
0.7629	Intermediate Similarity	NPD6079	Approved
0.7619	Intermediate Similarity	NPD6881	Approved
0.7619	Intermediate Similarity	NPD6899	Approved
0.7619	Intermediate Similarity	NPD7320	Approved
0.76	Intermediate Similarity	NPD4755	Approved
0.757	Intermediate Similarity	NPD6650	Approved
0.757	Intermediate Similarity	NPD6649	Approved
0.7525	Intermediate Similarity	NPD7638	Approved
0.7524	Intermediate Similarity	NPD5701	Approved
0.7524	Intermediate Similarity	NPD5697	Approved
0.75	Intermediate Similarity	NPD4697	Phase 3
0.75	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7477	Intermediate Similarity	NPD6883	Approved
0.7477	Intermediate Similarity	NPD7290	Approved
0.7477	Intermediate Similarity	NPD7102	Approved
0.7453	Intermediate Similarity	NPD6011	Approved
0.7451	Intermediate Similarity	NPD5285	Approved
0.7451	Intermediate Similarity	NPD7639	Approved
0.7451	Intermediate Similarity	NPD5286	Approved
0.7451	Intermediate Similarity	NPD4700	Approved
0.7451	Intermediate Similarity	NPD4696	Approved
0.7451	Intermediate Similarity	NPD7640	Approved
0.7449	Intermediate Similarity	NPD6411	Approved
0.7447	Intermediate Similarity	NPD3665	Phase 1
0.7447	Intermediate Similarity	NPD3666	Approved
0.7447	Intermediate Similarity	NPD3668	Phase 3
0.7447	Intermediate Similarity	NPD3133	Approved
0.7444	Intermediate Similarity	NPD6116	Phase 1
0.7426	Intermediate Similarity	NPD6083	Phase 2
0.7426	Intermediate Similarity	NPD6084	Phase 2
0.7407	Intermediate Similarity	NPD8130	Phase 1
0.7407	Intermediate Similarity	NPD6617	Approved
0.7407	Intermediate Similarity	NPD6847	Approved
0.7407	Intermediate Similarity	NPD6869	Approved
0.7407	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD3573	Approved
0.7387	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7387	Intermediate Similarity	NPD7115	Discovery
0.7383	Intermediate Similarity	NPD6013	Approved
0.7383	Intermediate Similarity	NPD6012	Approved
0.7383	Intermediate Similarity	NPD6014	Approved
0.7383	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD5223	Approved
0.7339	Intermediate Similarity	NPD6882	Approved
0.7339	Intermediate Similarity	NPD8297	Approved
0.7333	Intermediate Similarity	NPD6117	Approved
0.7327	Intermediate Similarity	NPD5222	Approved
0.7327	Intermediate Similarity	NPD5221	Approved
0.7327	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD5225	Approved
0.7308	Intermediate Similarity	NPD4633	Approved
0.7308	Intermediate Similarity	NPD5226	Approved
0.7308	Intermediate Similarity	NPD5224	Approved
0.7308	Intermediate Similarity	NPD5211	Phase 2
0.7304	Intermediate Similarity	NPD8328	Phase 3
0.7292	Intermediate Similarity	NPD6684	Approved
0.7292	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD7146	Approved
0.7292	Intermediate Similarity	NPD6409	Approved
0.7292	Intermediate Similarity	NPD5330	Approved
0.7292	Intermediate Similarity	NPD7334	Approved
0.7292	Intermediate Similarity	NPD7521	Approved
0.7273	Intermediate Similarity	NPD5284	Approved
0.7273	Intermediate Similarity	NPD5281	Approved
0.7264	Intermediate Similarity	NPD6008	Approved
0.7255	Intermediate Similarity	NPD5173	Approved
0.7245	Intermediate Similarity	NPD6101	Approved
0.7245	Intermediate Similarity	NPD4753	Phase 2
0.7245	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD4754	Approved
0.7238	Intermediate Similarity	NPD5174	Approved
0.7238	Intermediate Similarity	NPD5175	Approved
0.7228	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD6942	Approved
0.7222	Intermediate Similarity	NPD7339	Approved
0.7204	Intermediate Similarity	NPD4695	Discontinued
0.7184	Intermediate Similarity	NPD5696	Approved
0.7174	Intermediate Similarity	NPD6118	Approved
0.7174	Intermediate Similarity	NPD6115	Approved
0.7174	Intermediate Similarity	NPD6114	Approved
0.7174	Intermediate Similarity	NPD6697	Approved
0.717	Intermediate Similarity	NPD5141	Approved
0.7157	Intermediate Similarity	NPD7614	Phase 1
0.7143	Intermediate Similarity	NPD6903	Approved
0.7143	Intermediate Similarity	NPD6672	Approved
0.7143	Intermediate Similarity	NPD5737	Approved
0.7143	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD4632	Approved
0.7111	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD4767	Approved
0.7103	Intermediate Similarity	NPD4768	Approved
0.7059	Intermediate Similarity	NPD4629	Approved
0.7059	Intermediate Similarity	NPD5695	Phase 3
0.7059	Intermediate Similarity	NPD5210	Approved
0.7053	Intermediate Similarity	NPD4221	Approved
0.7053	Intermediate Similarity	NPD4223	Phase 3
0.7019	Intermediate Similarity	NPD4225	Approved
0.7018	Intermediate Similarity	NPD6335	Approved
0.701	Intermediate Similarity	NPD5329	Approved
0.6991	Remote Similarity	NPD6274	Approved
0.6979	Remote Similarity	NPD4788	Approved
0.6972	Remote Similarity	NPD4729	Approved
0.6972	Remote Similarity	NPD4730	Approved
0.6972	Remote Similarity	NPD5128	Approved
0.6957	Remote Similarity	NPD7100	Approved
0.6957	Remote Similarity	NPD7101	Approved
0.6939	Remote Similarity	NPD5279	Phase 3
0.6939	Remote Similarity	NPD6098	Approved
0.693	Remote Similarity	NPD6009	Approved
0.693	Remote Similarity	NPD6317	Approved
0.6909	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD4197	Approved
0.69	Remote Similarity	NPD6080	Approved
0.69	Remote Similarity	NPD6673	Approved
0.69	Remote Similarity	NPD6904	Approved
0.6881	Remote Similarity	NPD6412	Phase 2
0.687	Remote Similarity	NPD6313	Approved
0.687	Remote Similarity	NPD6314	Approved
0.6863	Remote Similarity	NPD5778	Approved
0.6863	Remote Similarity	NPD5779	Approved
0.6847	Remote Similarity	NPD5247	Approved
0.6847	Remote Similarity	NPD5135	Approved
0.6847	Remote Similarity	NPD5169	Approved
0.6847	Remote Similarity	NPD5248	Approved
0.6847	Remote Similarity	NPD4634	Approved
0.6847	Remote Similarity	NPD5249	Phase 3
0.6847	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD5251	Approved
0.6847	Remote Similarity	NPD5250	Approved
0.6847	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD6868	Approved
0.6838	Remote Similarity	NPD6909	Approved
0.6838	Remote Similarity	NPD6908	Approved
0.6838	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6827	Remote Similarity	NPD7732	Phase 3
0.6822	Remote Similarity	NPD7632	Discontinued
0.6818	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD8133	Approved
0.6796	Remote Similarity	NPD6001	Approved
0.6786	Remote Similarity	NPD5215	Approved
0.6786	Remote Similarity	NPD5127	Approved
0.6786	Remote Similarity	NPD5216	Approved
0.6786	Remote Similarity	NPD5217	Approved
0.6777	Remote Similarity	NPD7736	Approved
0.6771	Remote Similarity	NPD5369	Approved
0.6768	Remote Similarity	NPD4623	Approved
0.6768	Remote Similarity	NPD4690	Approved
0.6768	Remote Similarity	NPD4519	Discontinued
0.6768	Remote Similarity	NPD4689	Approved
0.6768	Remote Similarity	NPD5205	Approved
0.6768	Remote Similarity	NPD4693	Phase 3
0.6768	Remote Similarity	NPD4138	Approved
0.6768	Remote Similarity	NPD4688	Approved
0.6752	Remote Similarity	NPD6319	Approved
0.675	Remote Similarity	NPD7507	Approved
0.6739	Remote Similarity	NPD6926	Approved
0.6739	Remote Similarity	NPD6924	Approved
0.6723	Remote Similarity	NPD7604	Phase 2
0.6703	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD5983	Phase 2
0.6667	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7492	Approved
0.6667	Remote Similarity	NPD6686	Approved
0.6667	Remote Similarity	NPD7509	Discontinued
0.6667	Remote Similarity	NPD1694	Approved
0.6667	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5168	Approved
0.6634	Remote Similarity	NPD5208	Approved
0.6632	Remote Similarity	NPD3617	Approved
0.6632	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD6336	Discontinued
0.6612	Remote Similarity	NPD6616	Approved
0.661	Remote Similarity	NPD6059	Approved
0.661	Remote Similarity	NPD6054	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data