NPASS Compound

Structure

CID180199 OpenBabel06191715552D 24 27 0 0 1 0 0 0 0 0999 V2000 -1.5369 -0.8610 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8750 2.0766 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0739 -0.0001 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0001 -1.7748 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7684 -1.3311 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7685 1.3310 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3054 -0.4437 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0739 0.8873 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 0.8874 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7685 -0.4437 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8874 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8619 -0.5626 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7685 -1.3311 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5370 0.8873 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7685 -0.4437 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.7359 2.0766 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5369 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.3054 1.3310 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.2122 -0.5626 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.9970 0.0729 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3055 2.8222 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5969 2.0766 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6397 -1.3029 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3 7 1 0 0 0 0 3 8 1 0 0 0 0 4 5 1 0 0 0 0 4 13 1 0 0 0 0 5 15 1 0 0 0 0 6 9 1 0 0 0 0 6 14 1 0 0 0 0 7 17 1 0 0 0 0 8 18 1 0 0 0 0 10 13 1 0 0 0 0 10 19 1 0 0 0 0 11 19 1 0 0 0 0 11 20 1 0 0 0 0 12 20 1 0 0 0 0 12 21 1 0 0 0 0 13 20 1 6 0 0 0 14 17 1 1 0 0 0 14 18 1 0 0 0 0 15 17 1 1 0 0 0 15 19 1 0 0 0 0 16 18 1 0 0 0 0 16 22 2 0 0 0 0 16 23 1 0 0 0 0 17 1 1 1 0 0 0 18 2 1 6 0 0 0 19 9 1 1 0 0 0 20 24 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	336.23
Volume:	352.775
LogP:	1.553
LogD:	1.85
LogS:	-3.105
# Rotatable Bonds:	2
TPSA:	77.76
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.723
Synthetic Accessibility Score:	5.644
Fsp3:	0.95
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.681
MDCK Permeability:	7.231607014546171e-06
Pgp-inhibitor:	0.19
Pgp-substrate:	0.064
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.014
30% Bioavailability (F30%):	0.934

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.358
Plasma Protein Binding (PPB):	87.25743865966797%
Volume Distribution (VD):	0.452
Pgp-substrate:	11.404633522033691%

ADMET: Metabolism

CYP1A2-inhibitor:	0.006
CYP1A2-substrate:	0.795
CYP2C19-inhibitor:	0.008
CYP2C19-substrate:	0.579
CYP2C9-inhibitor:	0.029
CYP2C9-substrate:	0.089
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.117
CYP3A4-inhibitor:	0.604
CYP3A4-substrate:	0.067

ADMET: Excretion

Clearance (CL):	1.901
Half-life (T1/2):	0.48

ADMET: Toxicity

hERG Blockers:	0.036
Human Hepatotoxicity (H-HT):	0.654
Drug-inuced Liver Injury (DILI):	0.026
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.016
Maximum Recommended Daily Dose:	0.549
Skin Sensitization:	0.667
Carcinogencity:	0.559
Eye Corrosion:	0.075
Eye Irritation:	0.161
Respiratory Toxicity:	0.948

Download Data

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

Natural Product: NPC180199

Natural Product ID:	NPC180199
*Common Name:**	MRBLTWPEPGRXQN-WMUQSPHGSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	MRBLTWPEPGRXQN-WMUQSPHGSA-N
Standard InCHI:	InChI=1S/C20H32O4/c1-17-7-3-8-18(2,16(22)23)14(17)6-9-19-10-13(4-5-15(17)19)20(24,11-19)12-21/h13-15,21,24H,3-12H2,1-2H3,(H,22,23)/t13-,14+,15+,17-,18-,19+,20-/m1/s1
SMILES:	OC[C@]1(O)C[C@@]23C[C@H]1CC[C@H]3[C@]1([C@H](CC2)[C@@](C)(CCC1)C(=O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL482613
PubChem CID:	469209
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0003782] Kaurane diterpenoids

*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
NPO30302	Helianthus	Genus	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0031-9422(00)80485-9]
NPO15810	Zea mays	Species	Poaceae	Eukaryota		n.a.	n.a.	DOI[10.1021/jf00055a023]
NPO6333	Annona glabra	Species	Annonaceae	Eukaryota	n.a.	stem wood	n.a.	DOI[10.1021/np100247r]
NPO9632	Annona reticulata	Species	Annonaceae	Eukaryota	n.a.	stem	n.a.	DOI[10.1021/np50053a043]
NPO19242	Eucalyptus albens	Species	Myrtaceae	Eukaryota	flowers	n.a.	n.a.	PMID[10075775]
NPO6333	Annona glabra	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10395501]
NPO6333	Annona glabra	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10425140]
NPO11164	Renealmia alpinia	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10479331]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	seeds	n.a.	n.a.	PMID[11141125]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	n.a.	seed	n.a.	PMID[11539687]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12398544]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12713418]
NPO19436	Annona cherimola	Species	Annonaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[15387664]
NPO6333	Annona glabra	Species	Annonaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[15568797]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18419154]
NPO19083	Alstonia angustiloba	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18524603]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19296389]
NPO6333	Annona glabra	Species	Annonaceae	Eukaryota	stem	Taipei Botanical Garden, Taipei, Taiwan, China	2006-MAR	PMID[20828184]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21080643]
NPO17759	Rhododendron mucronulatum	Species	Ericaceae	Eukaryota	n.a.	stem	n.a.	PMID[21443171]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	n.a.	leaf	n.a.	PMID[21574561]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	n.a.	husk	n.a.	PMID[21574561]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21910504]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	seed	n.a.	PMID[22011319]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	seeds	n.a.	n.a.	PMID[22011319]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	n.a.	seed	n.a.	PMID[23292602]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	Barks	n.a.	n.a.	PMID[2348205]
NPO18602	Melampodium leucanthum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23501116]
NPO6333	Annona glabra	Species	Annonaceae	Eukaryota	fruits	n.a.	n.a.	PMID[25499882]
NPO18602	Melampodium leucanthum	Species	Asteraceae	Eukaryota	leaves and branches	San Antonio, Texas	2004-JUN	PMID[25685941]
NPO18602	Melampodium leucanthum	Species	Asteraceae	Eukaryota	leaves and branches	n.a.	n.a.	PMID[25685941]
NPO17296	Beesia calthifolia	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26238319]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29762032]
NPO18676	Clerodendrum trichotomum	Species	Lamiaceae	Eukaryota	Roots	n.a.	n.a.	PMID[29924604]
NPO9632	Annona reticulata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8277309]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	fruit	n.a.	PMID[8786370]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	n.a.	pollen	n.a.	PMID[8987503]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	bark	n.a.	n.a.	PMID[9214729]
NPO11164	Renealmia alpinia	Species	Zingiberaceae	Eukaryota	n.a.	Suriname rainforest	n.a.	PMID[9428162]
NPO6333	Annona glabra	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9584397]
NPO6333	Annona glabra	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9599260]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	Husk Essent. Oil	n.a.	n.a.	Database[FooDB]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	Oil	n.a.	n.a.	Database[FooDB]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	Pollen Or Spore	n.a.	n.a.	Database[FooDB]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO19436	Annona cherimola	Species	Annonaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	Seed Essent. Oil	n.a.	n.a.	Database[FooDB]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO15810	Zea mays	Species	Poaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	Silk Essent. Oil	n.a.	n.a.	Database[FooDB]
NPO19436	Annona cherimola	Species	Annonaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	Silk Stigma Style	n.a.	n.a.	Database[FooDB]
NPO9632	Annona reticulata	Species	Annonaceae	Eukaryota	Bark	n.a.	n.a.	Database[FooDB]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	Stem	n.a.	n.a.	Database[FooDB]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	Cob	n.a.	n.a.	Database[FooDB]
NPO9632	Annona reticulata	Species	Annonaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO19436	Annona cherimola	Species	Annonaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO9632	Annona reticulata	Species	Annonaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO19436	Annona cherimola	Species	Annonaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO9632	Annona reticulata	Species	Annonaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO9632	Annona reticulata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1783	Euonymus fortunei	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19769	Boschniakia rossica	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13737	Tephroseris kirilowii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6333	Annona glabra	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17759	Rhododendron mucronulatum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18765	Juniperus scopulorum	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18676	Clerodendrum trichotomum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1783	Euonymus fortunei	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11967	Delphinium giraldii	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13737	Tephroseris kirilowii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18765	Juniperus scopulorum	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17296	Beesia calthifolia	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6333	Annona glabra	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13358	Piper brachystachyum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9632	Annona reticulata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14233	Ormosia dasycarpa	Species	Limoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17759	Rhododendron mucronulatum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24402.1	Coffea liberica var. dewevrei	Varieties	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19769	Boschniakia rossica	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17759	Rhododendron mucronulatum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9632	Annona reticulata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO19769	Boschniakia rossica	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18765	Juniperus scopulorum	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO15127	Senecio congestus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11646	Morella pensylvanica	Species	Myricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18262	Aspergillus microcysticus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12914	Sarcophyton flexuosum	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17296	Beesia calthifolia	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19083	Alstonia angustiloba	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29531	Lupinus cosentinii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17499	Bursera kerberi	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11164	Renealmia alpinia	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19572	Pellacalyx axillaris	Species	Rhizophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9632	Annona reticulata	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17354	Micromonospora echinospora	Species	Micromonosporaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO17230	Psidium acutangulum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11967	Delphinium giraldii	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19709	Pseudocyphellaria australiensis	Species	Lobariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17759	Rhododendron mucronulatum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19242	Eucalyptus albens	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18424	Selinum libanotis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13358	Piper brachystachyum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19769	Boschniakia rossica	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19371	Costasiella ocellifera	Species	Costasiellidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18348	Crotalaria stolzii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11081	Baccharis grandicapitulata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18048	Phlomis crinita	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8172	Emericellopsis minima	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4679	Hedysarum gmelini	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17630	Helenium integrifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18533	Delisea elegans	Species	Bonnemaisoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6333	Annona glabra	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19170	Lasianthaea podocephala	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO968	Artemisia pectinata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18927	Clinacanthus nutans	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9906	Zephyranthes flava	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17114	Streptomyces melanogenes	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO25370	Botrychium ternatum	Species	Ophioglossaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5455	Euploca racemosa	Species	Heliotropiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16135	Pestalotiopsis oenotherae	Species	Sporocadaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1783	Euonymus fortunei	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24402.1	Coffea liberica var. dewevrei	Varieties	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16325	Sideritis dasygnaphala	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15810	Zea mays	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29450	Streptomyces parvisporogenes	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO12223	Stellaria media	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19436	Annona cherimola	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18676	Clerodendrum trichotomum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12870	Curcuma aeruginosa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15802	Papaver pseudocanescens	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14233	Ormosia dasycarpa	Species	Limoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13737	Tephroseris kirilowii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18765	Juniperus scopulorum	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18169	Creosphaeria sassafras	Species	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18602	Melampodium leucanthum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16981	Gutierrezia dracunculoides	Species	Asteraceae	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	1
IC50	1
Others	6

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	4
Organism	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	14320.0	nM	PMID[475108]
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	70.4	%	PMID[475108]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	14.9	%	PMID[475106]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	8.6	%	PMID[475106]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	14.4	%	PMID[475106]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	6.8	%	PMID[475106]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	0.8	ug.mL-1	PMID[475107]
NPT27	Others	Unspecified		Ratio	>	5.0	n.a.	PMID[475107]

☑ 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 NPC180199 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	319
0.1-0.2	3098
0.2-0.3	14435
0.3-0.4	9445
0.4-0.5	5941
0.5-0.6	5453
0.6-0.7	3258
0.7-0.8	608
0.8-0.85	61
0.85-0.9	58
0.9-0.95	17
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC477919
0.9861	High Similarity	NPC476732
0.9861	High Similarity	NPC199965
0.9342	High Similarity	NPC477935
0.9333	High Similarity	NPC472853
0.9306	High Similarity	NPC472854
0.9178	High Similarity	NPC24014
0.9178	High Similarity	NPC27349
0.9091	High Similarity	NPC477936
0.9014	High Similarity	NPC319671
0.9014	High Similarity	NPC469941
0.9014	High Similarity	NPC476734
0.9014	High Similarity	NPC252032
0.8974	High Similarity	NPC259173
0.8961	High Similarity	NPC12933
0.8889	High Similarity	NPC477929
0.8875	High Similarity	NPC472272
0.88	High Similarity	NPC4209
0.8784	High Similarity	NPC280026
0.8784	High Similarity	NPC167702
0.8784	High Similarity	NPC477930
0.8767	High Similarity	NPC469940
0.8684	High Similarity	NPC474404
0.8684	High Similarity	NPC171658
0.8684	High Similarity	NPC207010
0.8684	High Similarity	NPC264602
0.8684	High Similarity	NPC317913
0.8667	High Similarity	NPC212733
0.8667	High Similarity	NPC472311
0.8649	High Similarity	NPC310766
0.863	High Similarity	NPC477850
0.8608	High Similarity	NPC317066
0.8608	High Similarity	NPC121121
0.8592	High Similarity	NPC477931
0.8592	High Similarity	NPC42060
0.8592	High Similarity	NPC268736
0.859	High Similarity	NPC470609
0.8571	High Similarity	NPC224802
0.8571	High Similarity	NPC80089
0.8571	High Similarity	NPC171426
0.8571	High Similarity	NPC34046
0.8571	High Similarity	NPC324700
0.8571	High Similarity	NPC185465
0.8553	High Similarity	NPC477933
0.8553	High Similarity	NPC477932
0.8493	Intermediate Similarity	NPC324607
0.8493	Intermediate Similarity	NPC196197
0.8493	Intermediate Similarity	NPC321732
0.8493	Intermediate Similarity	NPC64466
0.8462	Intermediate Similarity	NPC320144
0.8462	Intermediate Similarity	NPC201276
0.8462	Intermediate Similarity	NPC80891
0.8462	Intermediate Similarity	NPC472310
0.8451	Intermediate Similarity	NPC190827
0.8451	Intermediate Similarity	NPC243469
0.8451	Intermediate Similarity	NPC475943
0.8442	Intermediate Similarity	NPC143133
0.8442	Intermediate Similarity	NPC298168
0.8442	Intermediate Similarity	NPC477918
0.8421	Intermediate Similarity	NPC477934
0.8415	Intermediate Similarity	NPC92139
0.8378	Intermediate Similarity	NPC108131
0.8375	Intermediate Similarity	NPC100366
0.8375	Intermediate Similarity	NPC242771
0.8375	Intermediate Similarity	NPC311642
0.8375	Intermediate Similarity	NPC164289
0.8333	Intermediate Similarity	NPC476733
0.8333	Intermediate Similarity	NPC215029
0.8333	Intermediate Similarity	NPC329117
0.8272	Intermediate Similarity	NPC245866
0.8267	Intermediate Similarity	NPC58057
0.8267	Intermediate Similarity	NPC156277
0.8267	Intermediate Similarity	NPC320549
0.8267	Intermediate Similarity	NPC151018
0.825	Intermediate Similarity	NPC77311
0.825	Intermediate Similarity	NPC58631
0.8243	Intermediate Similarity	NPC474962
0.8219	Intermediate Similarity	NPC478180
0.8219	Intermediate Similarity	NPC63190
0.8219	Intermediate Similarity	NPC474221
0.8219	Intermediate Similarity	NPC130459
0.8214	Intermediate Similarity	NPC33398
0.8193	Intermediate Similarity	NPC476727
0.8193	Intermediate Similarity	NPC476726
0.8193	Intermediate Similarity	NPC80590
0.8193	Intermediate Similarity	NPC474448
0.8161	Intermediate Similarity	NPC206878
0.8161	Intermediate Similarity	NPC470423
0.8158	Intermediate Similarity	NPC232112
0.8148	Intermediate Similarity	NPC102156
0.8148	Intermediate Similarity	NPC289486
0.8148	Intermediate Similarity	NPC328007
0.8148	Intermediate Similarity	NPC61107
0.8148	Intermediate Similarity	NPC30583
0.8148	Intermediate Similarity	NPC148740
0.8125	Intermediate Similarity	NPC261616
0.8118	Intermediate Similarity	NPC24705
0.8118	Intermediate Similarity	NPC56962
0.8108	Intermediate Similarity	NPC473225
0.8101	Intermediate Similarity	NPC471045
0.8095	Intermediate Similarity	NPC134197
0.8068	Intermediate Similarity	NPC215570
0.8052	Intermediate Similarity	NPC472945
0.8052	Intermediate Similarity	NPC472944
0.8052	Intermediate Similarity	NPC254340
0.8049	Intermediate Similarity	NPC472744
0.8049	Intermediate Similarity	NPC268578
0.8049	Intermediate Similarity	NPC327451
0.8049	Intermediate Similarity	NPC217559
0.8049	Intermediate Similarity	NPC292458
0.8026	Intermediate Similarity	NPC473267
0.8026	Intermediate Similarity	NPC472309
0.8025	Intermediate Similarity	NPC469745
0.8	Intermediate Similarity	NPC213178
0.8	Intermediate Similarity	NPC131892
0.8	Intermediate Similarity	NPC255176
0.8	Intermediate Similarity	NPC183374
0.8	Intermediate Similarity	NPC211162
0.8	Intermediate Similarity	NPC327728
0.8	Intermediate Similarity	NPC6120
0.8	Intermediate Similarity	NPC31302
0.8	Intermediate Similarity	NPC245029
0.7978	Intermediate Similarity	NPC116683
0.7976	Intermediate Similarity	NPC475007
0.7975	Intermediate Similarity	NPC23884
0.7975	Intermediate Similarity	NPC475031
0.7975	Intermediate Similarity	NPC66105
0.7952	Intermediate Similarity	NPC473336
0.7952	Intermediate Similarity	NPC263974
0.7952	Intermediate Similarity	NPC471044
0.7949	Intermediate Similarity	NPC195155
0.7949	Intermediate Similarity	NPC174964
0.7949	Intermediate Similarity	NPC179858
0.7949	Intermediate Similarity	NPC273366
0.7949	Intermediate Similarity	NPC97534
0.7949	Intermediate Similarity	NPC21220
0.7949	Intermediate Similarity	NPC125767
0.7927	Intermediate Similarity	NPC170985
0.7922	Intermediate Similarity	NPC153719
0.7922	Intermediate Similarity	NPC81759
0.7907	Intermediate Similarity	NPC116146
0.7907	Intermediate Similarity	NPC24772
0.7907	Intermediate Similarity	NPC220498
0.7901	Intermediate Similarity	NPC477851
0.7895	Intermediate Similarity	NPC476731
0.7867	Intermediate Similarity	NPC478228
0.7865	Intermediate Similarity	NPC470031
0.7857	Intermediate Similarity	NPC266651
0.7857	Intermediate Similarity	NPC201655
0.7848	Intermediate Similarity	NPC472486
0.7848	Intermediate Similarity	NPC5767
0.7848	Intermediate Similarity	NPC472487
0.7848	Intermediate Similarity	NPC475742
0.7848	Intermediate Similarity	NPC246445
0.7841	Intermediate Similarity	NPC472231
0.7841	Intermediate Similarity	NPC472232
0.7816	Intermediate Similarity	NPC77756
0.7792	Intermediate Similarity	NPC197701
0.7792	Intermediate Similarity	NPC478227
0.7792	Intermediate Similarity	NPC89310
0.7778	Intermediate Similarity	NPC52951
0.7778	Intermediate Similarity	NPC476176
0.7765	Intermediate Similarity	NPC80700
0.7765	Intermediate Similarity	NPC2783
0.7765	Intermediate Similarity	NPC472745
0.7765	Intermediate Similarity	NPC70661
0.7765	Intermediate Similarity	NPC472505
0.7765	Intermediate Similarity	NPC302111
0.7763	Intermediate Similarity	NPC107919
0.7753	Intermediate Similarity	NPC470424
0.775	Intermediate Similarity	NPC221420
0.7738	Intermediate Similarity	NPC319909
0.7733	Intermediate Similarity	NPC41542
0.7727	Intermediate Similarity	NPC52756
0.7722	Intermediate Similarity	NPC317242
0.7711	Intermediate Similarity	NPC154043
0.7711	Intermediate Similarity	NPC268040
0.7711	Intermediate Similarity	NPC202688
0.7711	Intermediate Similarity	NPC60018
0.7703	Intermediate Similarity	NPC472946
0.7703	Intermediate Similarity	NPC230047
0.7703	Intermediate Similarity	NPC19311
0.7692	Intermediate Similarity	NPC470610
0.7674	Intermediate Similarity	NPC269360
0.7674	Intermediate Similarity	NPC202937
0.7674	Intermediate Similarity	NPC264005
0.7674	Intermediate Similarity	NPC239938
0.7674	Intermediate Similarity	NPC33768
0.7674	Intermediate Similarity	NPC263802
0.7674	Intermediate Similarity	NPC252714
0.7654	Intermediate Similarity	NPC26029
0.7654	Intermediate Similarity	NPC472608
0.7647	Intermediate Similarity	NPC131350
0.7647	Intermediate Similarity	NPC264317
0.7647	Intermediate Similarity	NPC294438
0.764	Intermediate Similarity	NPC476189
0.764	Intermediate Similarity	NPC291373
0.7632	Intermediate Similarity	NPC260319
0.7632	Intermediate Similarity	NPC2568
0.7632	Intermediate Similarity	NPC100917

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 NPC180199 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	352
0.1-0.2	3369
0.2-0.3	3692
0.3-0.4	1049
0.4-0.5	273
0.5-0.6	226
0.6-0.7	155
0.7-0.8	12
0.8-0.85	9
0.85-0.9	12
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.88	High Similarity	NPD6117	Approved
0.8784	High Similarity	NPD6113	Clinical (unspecified phase)
0.8684	High Similarity	NPD6116	Phase 1
0.8667	High Similarity	NPD3702	Approved
0.863	High Similarity	NPD4244	Approved
0.863	High Similarity	NPD4245	Approved
0.8571	High Similarity	NPD6115	Approved
0.8571	High Similarity	NPD6114	Approved
0.8571	High Similarity	NPD6118	Approved
0.8571	High Similarity	NPD6697	Approved
0.8514	High Similarity	NPD6081	Approved
0.8493	Intermediate Similarity	NPD3698	Phase 2
0.8378	Intermediate Similarity	NPD4789	Approved
0.8333	Intermediate Similarity	NPD4224	Phase 2
0.8267	Intermediate Similarity	NPD5777	Approved
0.8267	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.8267	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.8194	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.8108	Intermediate Similarity	NPD5360	Phase 3
0.8108	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7831	Intermediate Similarity	NPD4788	Approved
0.7763	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD4758	Discontinued
0.75	Intermediate Similarity	NPD3198	Approved
0.75	Intermediate Similarity	NPD3703	Phase 2
0.7439	Intermediate Similarity	NPD5364	Discontinued
0.7436	Intermediate Similarity	NPD4787	Phase 1
0.7312	Intermediate Similarity	NPD6083	Phase 2
0.7312	Intermediate Similarity	NPD6084	Phase 2
0.7229	Intermediate Similarity	NPD3671	Phase 1
0.7143	Intermediate Similarity	NPD8034	Phase 2
0.7143	Intermediate Similarity	NPD8035	Phase 2
0.7111	Intermediate Similarity	NPD4753	Phase 2
0.6932	Remote Similarity	NPD3665	Phase 1
0.6932	Remote Similarity	NPD4786	Approved
0.6932	Remote Similarity	NPD3666	Approved
0.6932	Remote Similarity	NPD3133	Approved
0.6915	Remote Similarity	NPD5695	Phase 3
0.6897	Remote Similarity	NPD4223	Phase 3
0.6897	Remote Similarity	NPD4221	Approved
0.6882	Remote Similarity	NPD6399	Phase 3
0.6875	Remote Similarity	NPD5696	Approved
0.6869	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD5329	Approved
0.6813	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD8418	Phase 2
0.68	Remote Similarity	NPD5739	Approved
0.68	Remote Similarity	NPD7128	Approved
0.68	Remote Similarity	NPD6402	Approved
0.68	Remote Similarity	NPD6675	Approved
0.6782	Remote Similarity	NPD4139	Approved
0.6782	Remote Similarity	NPD4692	Approved
0.6778	Remote Similarity	NPD7146	Approved
0.6778	Remote Similarity	NPD6684	Approved
0.6778	Remote Similarity	NPD5330	Approved
0.6778	Remote Similarity	NPD7521	Approved
0.6778	Remote Similarity	NPD7334	Approved
0.6778	Remote Similarity	NPD6409	Approved
0.6778	Remote Similarity	NPD6098	Approved
0.6774	Remote Similarity	NPD5284	Approved
0.6774	Remote Similarity	NPD5281	Approved
0.6742	Remote Similarity	NPD4197	Approved
0.6739	Remote Similarity	NPD6673	Approved
0.6739	Remote Similarity	NPD6080	Approved
0.6739	Remote Similarity	NPD6904	Approved
0.6737	Remote Similarity	NPD4629	Approved
0.6737	Remote Similarity	NPD5210	Approved
0.6705	Remote Similarity	NPD3667	Approved
0.6702	Remote Similarity	NPD4202	Approved
0.6667	Remote Similarity	NPD7909	Approved
0.6667	Remote Similarity	NPD7320	Approved
0.6667	Remote Similarity	NPD6928	Phase 2
0.6667	Remote Similarity	NPD6899	Approved
0.6667	Remote Similarity	NPD6881	Approved
0.663	Remote Similarity	NPD6903	Approved
0.663	Remote Similarity	NPD5737	Approved
0.663	Remote Similarity	NPD6672	Approved
0.6602	Remote Similarity	NPD6372	Approved
0.6602	Remote Similarity	NPD6373	Approved
0.6598	Remote Similarity	NPD4755	Approved
0.6596	Remote Similarity	NPD7515	Phase 2
0.6593	Remote Similarity	NPD4689	Approved
0.6593	Remote Similarity	NPD5205	Approved
0.6593	Remote Similarity	NPD4688	Approved
0.6593	Remote Similarity	NPD4690	Approved
0.6593	Remote Similarity	NPD4138	Approved
0.6593	Remote Similarity	NPD4693	Phase 3
0.6571	Remote Similarity	NPD8297	Approved
0.6569	Remote Similarity	NPD5697	Approved
0.6569	Remote Similarity	NPD5701	Approved
0.6562	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD5328	Approved
0.6538	Remote Similarity	NPD7102	Approved
0.6538	Remote Similarity	NPD6883	Approved
0.6538	Remote Similarity	NPD7290	Approved
0.6531	Remote Similarity	NPD7638	Approved
0.6509	Remote Similarity	NPD8133	Approved
0.6509	Remote Similarity	NPD4632	Approved
0.6505	Remote Similarity	NPD6011	Approved
0.6477	Remote Similarity	NPD7525	Registered
0.6476	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD6650	Approved
0.6476	Remote Similarity	NPD6847	Approved
0.6476	Remote Similarity	NPD6649	Approved
0.6476	Remote Similarity	NPD6869	Approved
0.6476	Remote Similarity	NPD8130	Phase 1
0.6476	Remote Similarity	NPD6617	Approved
0.6465	Remote Similarity	NPD7639	Approved
0.6465	Remote Similarity	NPD5285	Approved
0.6465	Remote Similarity	NPD4696	Approved
0.6465	Remote Similarity	NPD5286	Approved
0.6465	Remote Similarity	NPD7640	Approved
0.6465	Remote Similarity	NPD4700	Approved
0.6452	Remote Similarity	NPD5208	Approved
0.6442	Remote Similarity	NPD6014	Approved
0.6442	Remote Similarity	NPD6013	Approved
0.6442	Remote Similarity	NPD6012	Approved
0.6437	Remote Similarity	NPD4238	Approved
0.6437	Remote Similarity	NPD4802	Phase 2
0.6437	Remote Similarity	NPD3617	Approved
0.6421	Remote Similarity	NPD6079	Approved
0.6421	Remote Similarity	NPD5693	Phase 1
0.6421	Remote Similarity	NPD6050	Approved
0.6415	Remote Similarity	NPD6882	Approved
0.6413	Remote Similarity	NPD5690	Phase 2
0.6413	Remote Similarity	NPD5280	Approved
0.6413	Remote Similarity	NPD3618	Phase 1
0.6413	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6413	Remote Similarity	NPD4694	Approved
0.6408	Remote Similarity	NPD6412	Phase 2
0.64	Remote Similarity	NPD5223	Approved
0.6354	Remote Similarity	NPD8171	Discontinued
0.6351	Remote Similarity	NPD615	Clinical (unspecified phase)
0.6341	Remote Similarity	NPD6705	Phase 1
0.6337	Remote Similarity	NPD7632	Discontinued
0.6337	Remote Similarity	NPD5224	Approved
0.6337	Remote Similarity	NPD5226	Approved
0.6337	Remote Similarity	NPD5211	Phase 2
0.6337	Remote Similarity	NPD4633	Approved
0.6337	Remote Similarity	NPD5225	Approved
0.6316	Remote Similarity	NPD5692	Phase 3
0.631	Remote Similarity	NPD4243	Approved
0.6289	Remote Similarity	NPD7748	Approved
0.6275	Remote Similarity	NPD4754	Approved
0.6275	Remote Similarity	NPD5174	Approved
0.6275	Remote Similarity	NPD5175	Approved
0.625	Remote Similarity	NPD5694	Approved
0.625	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD6940	Discontinued
0.6238	Remote Similarity	NPD1700	Approved
0.6237	Remote Similarity	NPD5279	Phase 3
0.6226	Remote Similarity	NPD4634	Approved
0.6222	Remote Similarity	NPD5369	Approved
0.6214	Remote Similarity	NPD5141	Approved
0.6211	Remote Similarity	NPD6051	Approved
0.6211	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD6933	Approved
0.6196	Remote Similarity	NPD3668	Phase 3
0.6182	Remote Similarity	NPD7115	Discovery
0.6182	Remote Similarity	NPD6009	Approved
0.618	Remote Similarity	NPD4195	Approved
0.6174	Remote Similarity	NPD7507	Approved
0.6163	Remote Similarity	NPD4785	Approved
0.6163	Remote Similarity	NPD4784	Approved
0.6162	Remote Similarity	NPD5221	Approved
0.6162	Remote Similarity	NPD4697	Phase 3
0.6162	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6162	Remote Similarity	NPD5222	Approved
0.6161	Remote Similarity	NPD6319	Approved
0.6154	Remote Similarity	NPD6920	Discontinued
0.6154	Remote Similarity	NPD4767	Approved
0.6154	Remote Similarity	NPD4768	Approved
0.6146	Remote Similarity	NPD5207	Approved
0.6126	Remote Similarity	NPD6335	Approved
0.6122	Remote Similarity	NPD6001	Approved
0.6111	Remote Similarity	NPD4748	Discontinued
0.6111	Remote Similarity	NPD5368	Approved
0.61	Remote Similarity	NPD5173	Approved
0.61	Remote Similarity	NPD7902	Approved
0.6092	Remote Similarity	NPD6942	Approved
0.6092	Remote Similarity	NPD7339	Approved
0.6091	Remote Similarity	NPD6274	Approved
0.6087	Remote Similarity	NPD5362	Discontinued
0.6071	Remote Similarity	NPD7101	Approved
0.6071	Remote Similarity	NPD7100	Approved
0.6061	Remote Similarity	NPD5654	Approved
0.6055	Remote Similarity	NPD8298	Phase 2
0.6038	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6038	Remote Similarity	NPD5128	Approved
0.6038	Remote Similarity	NPD4730	Approved
0.6038	Remote Similarity	NPD4729	Approved
0.6036	Remote Similarity	NPD6317	Approved
0.602	Remote Similarity	NPD5133	Approved
0.6017	Remote Similarity	NPD7319	Approved
0.6	Remote Similarity	NPD7604	Phase 2

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