NPASS Compound

Structure

NPC244940 OpenBabel06302216042D 75 83 0 0 1 0 0 0 0 0999 V2000 3.4229 -2.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4229 -1.9762 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5671 -1.4821 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5671 -0.4940 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4229 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4229 0.9881 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2786 1.4821 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1343 0.9881 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.1343 2.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1343 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9900 -0.4940 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8457 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8457 0.9881 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 7.7014 1.4821 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 7.7014 0.4940 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5572 0.9881 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4129 1.4821 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4129 2.4702 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 8.5572 2.9643 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 9.0512 3.8200 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0631 3.8200 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5572 4.6757 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7014 2.4702 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.8457 2.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9900 2.4702 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9900 1.4821 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1343 1.9762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.2686 2.9643 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 11.1243 2.4702 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 11.9800 2.9643 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 12.8357 2.4702 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 12.8357 1.4821 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 11.9800 0.9881 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.1243 1.4821 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 13.6914 0.9881 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 13.6914 2.9643 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 11.9800 3.9524 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2786 -0.4940 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.2786 -1.4821 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1343 -1.9762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5671 0.4940 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5671 1.4821 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7114 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8557 0.4940 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8557 1.4821 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 1.9762 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8557 1.4821 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8557 0.4940 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7114 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7114 -0.9881 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5671 -1.4821 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4229 -0.9881 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2786 -1.4821 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.2786 -2.4702 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4229 -2.9643 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4229 -3.9524 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5671 -4.4464 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5671 -2.4702 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1343 -2.9643 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1343 -3.9524 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.9900 -4.4464 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.9900 -5.4345 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1343 -5.9286 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.2786 -5.4345 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4229 -5.9286 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2786 -4.4464 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1343 -6.9167 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.8457 -5.9286 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.8457 -3.9524 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1343 -0.9881 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4229 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7114 1.9762 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.9643 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7114 1.9762 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 1 1 6 0 0 0 2 3 1 0 0 0 0 2 39 1 0 0 0 0 3 4 1 0 0 0 0 4 5 1 0 0 0 0 5 38 1 0 0 0 0 5 6 1 0 0 0 0 5 41 1 1 0 0 0 6 7 1 0 0 0 0 7 8 1 0 0 0 0 8 26 1 0 0 0 0 8 9 1 6 0 0 0 8 10 1 0 0 0 0 10 11 2 0 0 0 0 11 12 1 0 0 0 0 13 12 1 1 0 0 0 13 14 1 0 0 0 0 13 26 1 0 0 0 0 14 23 1 0 0 0 0 14 15 1 1 0 0 0 14 16 1 0 0 0 0 16 17 1 0 0 0 0 17 18 1 0 0 0 0 18 19 1 0 0 0 0 18 28 1 1 0 0 0 19 20 1 1 0 0 0 19 21 1 0 0 0 0 19 23 1 0 0 0 0 21 22 1 0 0 0 0 23 24 1 1 0 0 0 24 25 1 0 0 0 0 25 26 1 0 0 0 0 26 27 1 1 0 0 0 29 28 1 1 0 0 0 29 30 1 0 0 0 0 29 34 1 0 0 0 0 30 31 1 0 0 0 0 30 37 1 6 0 0 0 31 32 1 0 0 0 0 31 36 1 1 0 0 0 32 33 1 0 0 0 0 32 35 1 1 0 0 0 33 34 1 0 0 0 0 38 10 1 6 0 0 0 38 39 1 0 0 0 0 39 40 1 1 0 0 0 41 42 2 0 0 0 0 41 43 1 0 0 0 0 44 43 1 6 0 0 0 44 45 1 0 0 0 0 44 72 1 0 0 0 0 45 46 1 0 0 0 0 45 75 1 1 0 0 0 46 47 1 0 0 0 0 46 74 1 6 0 0 0 47 48 1 0 0 0 0 47 73 1 1 0 0 0 48 49 1 6 0 0 0 48 72 1 0 0 0 0 49 50 1 0 0 0 0 51 50 1 6 0 0 0 51 52 1 0 0 0 0 51 58 1 0 0 0 0 52 53 1 0 0 0 0 52 71 1 1 0 0 0 53 54 1 0 0 0 0 53 70 1 6 0 0 0 54 55 1 0 0 0 0 54 59 1 1 0 0 0 55 56 1 6 0 0 0 55 58 1 0 0 0 0 56 57 1 0 0 0 0 60 59 1 6 0 0 0 60 61 1 0 0 0 0 60 66 1 0 0 0 0 61 62 1 0 0 0 0 61 69 1 1 0 0 0 62 63 1 0 0 0 0 62 68 1 1 0 0 0 63 64 1 0 0 0 0 63 67 1 6 0 0 0 64 65 1 1 0 0 0 64 66 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	1074.56
Volume:	1036.348
LogP:	2.079
LogD:	1.653
LogS:	-3.211
# Rotatable Bonds:	12
TPSA:	353.9
# H-Bond Aceptor:	22
# H-Bond Donor:	13
# Rings:	9
# Heavy Atoms:	22

MedChem Properties

QED Drug-Likeness Score:	0.063
Synthetic Accessibility Score:	6.833
Fsp3:	0.943
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.27
MDCK Permeability:	0.000192275780136697
Pgp-inhibitor:	0.141
Pgp-substrate:	0.819
Human Intestinal Absorption (HIA):	0.996
20% Bioavailability (F20%):	0.045
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.037
Plasma Protein Binding (PPB):	73.15593719482422%
Volume Distribution (VD):	-0.017
Pgp-substrate:	12.89539623260498%

ADMET: Metabolism

CYP1A2-inhibitor:	0.0
CYP1A2-substrate:	0.879
CYP2C19-inhibitor:	0.001
CYP2C19-substrate:	0.244
CYP2C9-inhibitor:	0.0
CYP2C9-substrate:	0.002
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.038
CYP3A4-inhibitor:	0.057
CYP3A4-substrate:	0.005

ADMET: Excretion

Clearance (CL):	0.173
Half-life (T1/2):	0.706

ADMET: Toxicity

hERG Blockers:	0.269
Human Hepatotoxicity (H-HT):	0.167
Drug-inuced Liver Injury (DILI):	0.02
AMES Toxicity:	0.088
Rat Oral Acute Toxicity:	0.103
Maximum Recommended Daily Dose:	0.037
Skin Sensitization:	0.056
Carcinogencity:	0.016
Eye Corrosion:	0.003
Eye Irritation:	0.007
Respiratory Toxicity:	0.801

Download Data

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

Natural Product: NPC244940

Natural Product ID:	NPC244940
*Common Name:**	FDSRWPZECMMOFD-LURBLWJMSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	FDSRWPZECMMOFD-LURBLWJMSA-N
Standard InCHI:	InChI=1S/C53H86O22/c1-22-10-15-53(48(67)75-47-41(65)37(61)35(59)28(72-47)20-69-44-42(66)38(62)43(27(18-54)71-44)74-46-40(64)36(60)33(57)24(3)70-46)17-16-51(6)25(32(53)23(22)2)8-9-30-49(4)13-12-31(73-45-39(63)34(58)26(56)19-68-45)50(5,21-55)29(49)11-14-52(30,51)7/h8,22-24,26-47,54-66H,9-21H2,1-7H3/t22-,23+,24+,26+,27-,28-,29-,30-,31+,32+,33+,34+,35-,36-,37+,38-,39-,40-,41-,42-,43-,44-,45+,46+,47+,49+,50+,51-,52-,53+/m1/s1
SMILES:	C[C@@H]1CC[C@@]2(CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)CC[C@@H]([C@@](C)(CO)[C@@H]5CC[C@@]34C)O[C@H]3[C@@H]([C@H]([C@H](CO3)O)O)O)[C@@H]2[C@H]1C)C(=O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO[C@H]2[C@@H]([C@H]([C@@H]([C@@H](CO)O2)O[C@H]2[C@@H]([C@@H]([C@H]([C@H](C)O2)O)O)O)O)O)O1)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	101675597
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides [CHEMONTID:0001580] Triterpene glycosides [CHEMONTID:0002358] Triterpene saponins

*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
NPO4359	Solanum tuberosum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0031-9422(00)89267-5]
NPO6003	Halorosellinia oceanica	Species	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11454459]
NPO4359	Solanum tuberosum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12882150]
NPO4359	Solanum tuberosum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15666542]
NPO10814	Ilex latifolia	Species	Aquifoliaceae	Eukaryota	n.a.	stem	n.a.	PMID[16252920]
NPO12610	Diospyros dendo	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16441080]
NPO3029	Daedalea dickinsii	Species	Coriolaceae	Eukaryota	n.a.	mycelium	n.a.	PMID[17986791]
NPO6003	Halorosellinia oceanica	Species	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO17954	Narcissus tazetta	Species	Amaryllidaceae	Eukaryota	n.a.	Turkey	n.a.	PMID[19299148]
NPO6003	Halorosellinia oceanica	Species	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21265556]
NPO4359	Solanum tuberosum	Species	Solanaceae	Eukaryota	n.a.	trunk bark	n.a.	PMID[556731]
NPO4359	Solanum tuberosum	Species	Solanaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO4359	Solanum tuberosum	Species	Solanaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO4359	Solanum tuberosum	Species	Solanaceae	Eukaryota	Tuber	n.a.	n.a.	Database[FooDB]
NPO22136	Hedysarum alpinum	Species	Fabaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO4359	Solanum tuberosum	Species	Solanaceae	Eukaryota	Tubers	n.a.		Database[FooDB]
NPO4359	Solanum tuberosum	Species	Solanaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO4359	Solanum tuberosum	Species	Solanaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO5200	Diphylleia grayi	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17954	Narcissus tazetta	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10814	Ilex latifolia	Species	Aquifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4359	Solanum tuberosum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29219	Primula veris	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4359	Solanum tuberosum	Species	Solanaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO10814	Ilex latifolia	Species	Aquifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17954	Narcissus tazetta	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4359	Solanum tuberosum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29219	Primula veris	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5200	Diphylleia grayi	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4359	Solanum tuberosum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5200	Diphylleia grayi	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15944	Primnoa resedaeformis	Species	Primnoidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4359	Solanum tuberosum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10814	Ilex latifolia	Species	Aquifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22136	Hedysarum alpinum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12836	Mentha javanica	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12019	Orontium japonicum	Species	Araceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5200	Diphylleia grayi	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13061	Balanocarpus zeylanicus	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO12781	Schefflera heptaphylla	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15495	Narcissus cantabricus	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29219	Primula veris	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1349	Zanthoxylum zanthoxyloides	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6003	Halorosellinia oceanica	Species	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17954	Narcissus tazetta	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3568	Myristica dactyloides	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12610	Diospyros dendo	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14426	Halictus sexcinctus	Species	Halictidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3029	Daedalea dickinsii	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10670	Bidens frondosa	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

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

☑ 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 NPC244940 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	261
0.1-0.2	1737
0.2-0.3	5108
0.3-0.4	11934
0.4-0.5	10269
0.5-0.6	6164
0.6-0.7	3984
0.7-0.8	1930
0.8-0.85	607
0.85-0.9	291
0.9-0.95	169
0.95-1	243

Similarity Score	Similarity Level	Natural Product ID

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 NPC244940 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	241
0.1-0.2	2042
0.2-0.3	3876
0.3-0.4	1952
0.4-0.5	598
0.5-0.6	266
0.6-0.7	142
0.7-0.8	21
0.8-0.85	8
0.85-0.9	3
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage

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