NPASS Compound

Structure

CID99264 OpenBabel06191715442D 39 43 0 0 1 0 0 0 0 0999 V2000 2.7544 -3.6421 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4772 1.4338 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9808 0.5752 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4863 0.5074 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0243 1.9284 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8773 -1.4640 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0003 -0.9852 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6579 2.8696 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2669 -2.9682 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6560 -3.8414 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6574 0.9575 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8284 1.4357 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1434 -1.4337 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6582 -1.9130 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6565 -0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4860 2.3909 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8292 2.3918 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1431 -0.4773 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8292 -1.4347 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8281 -0.4787 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4834 -5.4883 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3161 -2.8685 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3158 -1.9125 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4869 -1.4342 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.6069 -3.9411 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.4343 -5.5880 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6568 0.9565 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6577 0.0005 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0003 0.9570 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.9960 -4.8144 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4854 1.4343 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4866 -0.4778 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8287 1.4353 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8290 -0.4783 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 4.0943 -4.6151 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.1686 -3.1675 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8234 -6.4612 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9468 -4.9140 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 31 1 0 0 0 0 3 31 1 0 0 0 0 6 34 1 0 0 0 0 8 16 1 0 0 0 0 8 17 1 0 0 0 0 9 10 1 0 0 0 0 9 22 1 0 0 0 0 10 25 1 0 0 0 0 11 12 1 0 0 0 0 11 28 1 0 0 0 0 12 29 1 0 0 0 0 13 18 1 0 0 0 0 13 23 1 0 0 0 0 14 19 1 0 0 0 0 14 24 1 0 0 0 0 15 20 1 0 0 0 0 15 27 1 0 0 0 0 16 31 1 0 0 0 0 17 33 1 0 0 0 0 18 32 1 0 0 0 0 19 34 1 0 0 0 0 20 35 1 0 0 0 0 21 26 1 0 0 0 0 21 36 1 0 0 0 0 22 1 1 1 0 0 0 23 22 1 6 0 0 0 23 24 1 0 0 0 0 24 32 1 6 0 0 0 25 30 1 0 0 0 0 25 37 1 1 0 0 0 26 30 1 0 0 0 0 26 38 1 1 0 0 0 27 31 1 0 0 0 0 27 33 1 1 0 0 0 28 32 1 6 0 0 0 28 34 1 0 0 0 0 29 33 1 1 0 0 0 29 35 1 0 0 0 0 30 39 1 1 0 0 0 32 4 1 6 0 0 0 33 5 1 1 0 0 0 34 35 1 1 0 0 0 35 7 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	546.46
Volume:	606.295
LogP:	7.011
LogD:	5.773
LogS:	-5.688
# Rotatable Bonds:	7
TPSA:	80.92
# H-Bond Aceptor:	4
# H-Bond Donor:	4
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.278
Synthetic Accessibility Score:	5.072
Fsp3:	1.0
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.886
MDCK Permeability:	1.49762345245108e-05
Pgp-inhibitor:	0.849
Pgp-substrate:	0.011
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.901
30% Bioavailability (F30%):	0.792

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.026
Plasma Protein Binding (PPB):	91.88306427001953%
Volume Distribution (VD):	1.122
Pgp-substrate:	1.3890742063522339%

ADMET: Metabolism

CYP1A2-inhibitor:	0.018
CYP1A2-substrate:	0.352
CYP2C19-inhibitor:	0.027
CYP2C19-substrate:	0.947
CYP2C9-inhibitor:	0.092
CYP2C9-substrate:	0.394
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.702
CYP3A4-inhibitor:	0.216
CYP3A4-substrate:	0.213

ADMET: Excretion

Clearance (CL):	3.892
Half-life (T1/2):	0.117

ADMET: Toxicity

hERG Blockers:	0.827
Human Hepatotoxicity (H-HT):	0.14
Drug-inuced Liver Injury (DILI):	0.036
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.05
Maximum Recommended Daily Dose:	0.022
Skin Sensitization:	0.936
Carcinogencity:	0.015
Eye Corrosion:	0.25
Eye Irritation:	0.065
Respiratory Toxicity:	0.802

Download Data

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

Natural Product: NPC99264

Natural Product ID:	NPC99264
*Common Name:**	Tetrahydroxybacteriohopane
IUPAC Name:	(2S,3R,4R,7R)-7-[(3R,3aS,5aR,5bR,7aS,11aS,11bR,13aR,13bS)-5a,5b,8,8,11a,13b-hexamethyl-1,2,3,3a,4,5,6,7,7a,9,10,11,11b,12,13,13a-hexadecahydrocyclopenta[a]chrysen-3-yl]octane-1,2,3,4-tetrol
Synonyms:	Tetrahydroxybacteriohopane
Standard InCHIKey:	JMKBTQYGOKJMBJ-ZQPPIKFSSA-N
Standard InCHI:	InChI=1S/C35H62O4/c1-22(9-10-25(37)30(39)26(38)21-36)23-13-18-32(4)24(23)14-19-34(6)28(32)11-12-29-33(5)17-8-16-31(2,3)27(33)15-20-35(29,34)7/h22-30,36-39H,8-21H2,1-7H3/t22-,23-,24+,25-,26+,27+,28-,29-,30-,32+,33+,34-,35-/m1/s1
SMILES:	C[C@H](CC[C@H]([C@H]([C@H](CO)O)O)O)[C@H]1CC[C@@]2(C)[C@H]1CC[C@]1(C)[C@@H]2CC[C@@H]2[C@@]3(C)CCCC(C)(C)[C@@H]3CC[C@@]12C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL442840
PubChem CID:	11489675
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001823] Hopanoids [CHEMONTID:0001826] Bacteriohopanoids

*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
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[10344559]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[10344578]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[10348041]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[10604756]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[10695669]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[10724004]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[10994816]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11099231]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11132958]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11374972]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11473415]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[14738393]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	Australian	n.a.	PMID[15497950]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[15813185]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[15844966]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[15974616]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[16180833]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[1666120]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[16724845]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[16830891]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[16872146]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[17125235]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[17315965]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[17551212]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[17608531]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[17844998]
NPO1995	Rhodopseudomonas palustris	Species	Bradyrhizobiaceae	Bacteria	n.a.	n.a.	n.a.	PMID[17848515]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[17887721]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[17917237]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[18044841]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	Indonesian	n.a.	PMID[18081255]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[18081255]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[18205372]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[18327911]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	Northwest Territories, Canada	1995	PMID[18327911]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[18666798]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[18776684]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[19007176]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[19129624]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[19191549]
NPO30802	Desulfovibrio bastinii	Species	Desulfovibrionaceae	Bacteria	n.a.	n.a.	n.a.	PMID[19222571]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[19856955]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[19883065]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[20092333]
NPO1995	Rhodopseudomonas palustris	Species	Bradyrhizobiaceae	Bacteria	n.a.	n.a.	n.a.	PMID[20421508]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[20545334]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[20836523]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21028889]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21028891]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	mycelium	n.a.	PMID[21090727]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21314175]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	mycelium	n.a.	PMID[21639131]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21728289]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	latex	n.a.	PMID[21751787]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21807523]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21873059]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	latex	n.a.	PMID[21879726]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	mycelium	n.a.	PMID[22145663]
NPO1995	Rhodopseudomonas palustris	Species	Bradyrhizobiaceae	Bacteria	n.a.	n.a.	n.a.	PMID[22221333]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[22574670]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[22583058]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[22591466]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[22758660]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[22775474]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[23387796]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[23662937]
NPO30040	Ciceribacter lividus	Species	Rhizobiaceae	Bacteria	n.a.	n.a.	n.a.	PMID[23907221]
NPO1995	Rhodopseudomonas palustris	Species	Bradyrhizobiaceae	Bacteria	n.a.	n.a.	n.a.	PMID[24496464]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[24592993]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[24754815]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[24878306]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[24964393]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[25211234]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[25455147]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[25495422]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[25537064]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[25918793]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[25934225]
NPO11163	Methylobacterium organophilum	Species	Methylobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[26032177]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[26035239]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[26465675]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[26798949]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[26905826]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[31013087]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[31298537]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[31894983]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[32298122]
NPO11163	Methylobacterium organophilum	Species	Methylobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[3928379]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[8501018]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	mycelium	n.a.	PMID[8784423]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[8931733]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[8982334]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[9031666]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[9031676]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[9066767]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[9066768]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[9186568]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[9531983]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	mycelium	n.a.	PMID[9711246]
NPO1995	Rhodopseudomonas palustris	Species	Bradyrhizobiaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO11163	Methylobacterium organophilum	Species	Methylobacteriaceae	Bacteria	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
IC50	1
Others	9

Activity Type	# Activity
Individual Protein	2
Others	8

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT570	Individual Protein	Arachidonate 5-lipoxygenase	Homo sapiens	Activity	=	98.0	%	PMID[491473]
NPT570	Individual Protein	Arachidonate 5-lipoxygenase	Homo sapiens	Activity	=	97.0	%	PMID[491473]
NPT2	Others	Unspecified		IC50	=	10000.0	nM	PMID[491473]
NPT2	Others	Unspecified		Activity	=	68.0	%	PMID[491473]
NPT2	Others	Unspecified		Activity	=	48.0	%	PMID[491473]
NPT2	Others	Unspecified		Activity	=	15.0	%	PMID[491473]
NPT2	Others	Unspecified		Activity	=	4.0	%	PMID[491473]
NPT2	Others	Unspecified		Activity	=	11.0	%	PMID[491473]
NPT2	Others	Unspecified		Activity	=	102.0	%	PMID[491473]
NPT2	Others	Unspecified		Activity	=	103.0	%	PMID[491473]

☑ 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 NPC99264 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	381
0.1-0.2	4787
0.2-0.3	16782
0.3-0.4	8793
0.4-0.5	4795
0.5-0.6	4411
0.6-0.7	2058
0.7-0.8	608
0.8-0.85	67
0.85-0.9	14
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9077	High Similarity	NPC472946
0.8824	High Similarity	NPC107919
0.8696	High Similarity	NPC231945
0.8676	High Similarity	NPC472741
0.8657	High Similarity	NPC142712
0.8571	High Similarity	NPC127094
0.8529	High Similarity	NPC48079
0.8507	High Similarity	NPC190827
0.8507	High Similarity	NPC475943
0.8507	High Similarity	NPC243469
0.8485	Intermediate Similarity	NPC114891
0.8472	Intermediate Similarity	NPC158208
0.8472	Intermediate Similarity	NPC243027
0.8472	Intermediate Similarity	NPC317242
0.8472	Intermediate Similarity	NPC196136
0.8451	Intermediate Similarity	NPC470610
0.8438	Intermediate Similarity	NPC476735
0.8429	Intermediate Similarity	NPC192192
0.8356	Intermediate Similarity	NPC163597
0.8333	Intermediate Similarity	NPC228994
0.8333	Intermediate Similarity	NPC48795
0.8333	Intermediate Similarity	NPC71460
0.8333	Intermediate Similarity	NPC148174
0.8333	Intermediate Similarity	NPC10476
0.8333	Intermediate Similarity	NPC218585
0.8333	Intermediate Similarity	NPC192501
0.831	Intermediate Similarity	NPC157422
0.831	Intermediate Similarity	NPC100586
0.831	Intermediate Similarity	NPC109457
0.8286	Intermediate Similarity	NPC241085
0.8286	Intermediate Similarity	NPC299948
0.8286	Intermediate Similarity	NPC254037
0.8286	Intermediate Similarity	NPC66407
0.8286	Intermediate Similarity	NPC129829
0.8286	Intermediate Similarity	NPC470830
0.8261	Intermediate Similarity	NPC475884
0.8261	Intermediate Similarity	NPC63190
0.8261	Intermediate Similarity	NPC473230
0.8243	Intermediate Similarity	NPC105208
0.8243	Intermediate Similarity	NPC192046
0.8243	Intermediate Similarity	NPC185915
0.8243	Intermediate Similarity	NPC302578
0.8243	Intermediate Similarity	NPC477227
0.8243	Intermediate Similarity	NPC128951
0.8235	Intermediate Similarity	NPC260116
0.8194	Intermediate Similarity	NPC472341
0.8194	Intermediate Similarity	NPC153719
0.8194	Intermediate Similarity	NPC473238
0.8169	Intermediate Similarity	NPC251201
0.8169	Intermediate Similarity	NPC282454
0.8169	Intermediate Similarity	NPC232925
0.8169	Intermediate Similarity	NPC63588
0.8154	Intermediate Similarity	NPC162685
0.8133	Intermediate Similarity	NPC67657
0.8133	Intermediate Similarity	NPC147993
0.8133	Intermediate Similarity	NPC18857
0.8116	Intermediate Similarity	NPC44122
0.8088	Intermediate Similarity	NPC159654
0.8088	Intermediate Similarity	NPC167995
0.8088	Intermediate Similarity	NPC69149
0.8088	Intermediate Similarity	NPC281540
0.8088	Intermediate Similarity	NPC118937
0.8082	Intermediate Similarity	NPC472945
0.8082	Intermediate Similarity	NPC472944
0.8082	Intermediate Similarity	NPC304499
0.8056	Intermediate Similarity	NPC1340
0.8056	Intermediate Similarity	NPC470071
0.8056	Intermediate Similarity	NPC157777
0.8056	Intermediate Similarity	NPC131506
0.8056	Intermediate Similarity	NPC478103
0.8056	Intermediate Similarity	NPC187471
0.8056	Intermediate Similarity	NPC252182
0.8028	Intermediate Similarity	NPC477820
0.8028	Intermediate Similarity	NPC470833
0.8026	Intermediate Similarity	NPC287452
0.8026	Intermediate Similarity	NPC81074
0.8026	Intermediate Similarity	NPC477282
0.8	Intermediate Similarity	NPC474574
0.8	Intermediate Similarity	NPC133596
0.8	Intermediate Similarity	NPC264602
0.8	Intermediate Similarity	NPC64081
0.8	Intermediate Similarity	NPC11907
0.8	Intermediate Similarity	NPC204233
0.7971	Intermediate Similarity	NPC474380
0.7971	Intermediate Similarity	NPC473276
0.7971	Intermediate Similarity	NPC41577
0.7895	Intermediate Similarity	NPC102708
0.7887	Intermediate Similarity	NPC475893
0.7867	Intermediate Similarity	NPC477601
0.7867	Intermediate Similarity	NPC278091
0.7867	Intermediate Similarity	NPC473916
0.7867	Intermediate Similarity	NPC477602
0.7867	Intermediate Similarity	NPC470145
0.7867	Intermediate Similarity	NPC78067
0.7867	Intermediate Similarity	NPC86305
0.7867	Intermediate Similarity	NPC14112
0.7867	Intermediate Similarity	NPC93662
0.7848	Intermediate Similarity	NPC472744
0.7838	Intermediate Similarity	NPC478130
0.7838	Intermediate Similarity	NPC477508
0.7821	Intermediate Similarity	NPC73515
0.7808	Intermediate Similarity	NPC473279
0.7792	Intermediate Similarity	NPC220379
0.7733	Intermediate Similarity	NPC178383
0.7733	Intermediate Similarity	NPC212879
0.7733	Intermediate Similarity	NPC174964
0.7733	Intermediate Similarity	NPC270306
0.7733	Intermediate Similarity	NPC91387
0.7733	Intermediate Similarity	NPC104387
0.7733	Intermediate Similarity	NPC231256
0.7733	Intermediate Similarity	NPC195155
0.7733	Intermediate Similarity	NPC240235
0.7733	Intermediate Similarity	NPC97534
0.7733	Intermediate Similarity	NPC231680
0.7722	Intermediate Similarity	NPC154043
0.7722	Intermediate Similarity	NPC60018
0.7722	Intermediate Similarity	NPC202688
0.7722	Intermediate Similarity	NPC475388
0.7714	Intermediate Similarity	NPC80463
0.7703	Intermediate Similarity	NPC253805
0.7692	Intermediate Similarity	NPC475679
0.7692	Intermediate Similarity	NPC16449
0.7683	Intermediate Similarity	NPC43912
0.7683	Intermediate Similarity	NPC140446
0.7681	Intermediate Similarity	NPC290791
0.7681	Intermediate Similarity	NPC292419
0.7654	Intermediate Similarity	NPC290612
0.7639	Intermediate Similarity	NPC469987
0.7632	Intermediate Similarity	NPC5767
0.7632	Intermediate Similarity	NPC475742
0.7632	Intermediate Similarity	NPC91573
0.7625	Intermediate Similarity	NPC478054
0.7625	Intermediate Similarity	NPC85095
0.7625	Intermediate Similarity	NPC216420
0.7625	Intermediate Similarity	NPC211135
0.7625	Intermediate Similarity	NPC111582
0.7625	Intermediate Similarity	NPC477285
0.76	Intermediate Similarity	NPC62657
0.76	Intermediate Similarity	NPC25511
0.76	Intermediate Similarity	NPC472854
0.76	Intermediate Similarity	NPC192638
0.759	Intermediate Similarity	NPC281004
0.7568	Intermediate Similarity	NPC156277
0.7568	Intermediate Similarity	NPC195530
0.7568	Intermediate Similarity	NPC8004
0.7568	Intermediate Similarity	NPC127283
0.7568	Intermediate Similarity	NPC320549
0.7568	Intermediate Similarity	NPC151018
0.7568	Intermediate Similarity	NPC58057
0.7564	Intermediate Similarity	NPC475727
0.7564	Intermediate Similarity	NPC472742
0.7564	Intermediate Similarity	NPC116119
0.7564	Intermediate Similarity	NPC80297
0.7564	Intermediate Similarity	NPC269333
0.7561	Intermediate Similarity	NPC215968
0.7561	Intermediate Similarity	NPC471240
0.7561	Intermediate Similarity	NPC155531
0.7532	Intermediate Similarity	NPC207010
0.7532	Intermediate Similarity	NPC221420
0.7532	Intermediate Similarity	NPC317913
0.7532	Intermediate Similarity	NPC476233
0.7532	Intermediate Similarity	NPC202540
0.7532	Intermediate Similarity	NPC143133
0.7532	Intermediate Similarity	NPC248830
0.7532	Intermediate Similarity	NPC171658
0.7532	Intermediate Similarity	NPC298168
0.7532	Intermediate Similarity	NPC212241
0.7532	Intermediate Similarity	NPC119355
0.7532	Intermediate Similarity	NPC23884
0.7532	Intermediate Similarity	NPC180199
0.7532	Intermediate Similarity	NPC477919
0.7531	Intermediate Similarity	NPC227260
0.7531	Intermediate Similarity	NPC320824
0.7531	Intermediate Similarity	NPC255882
0.75	Intermediate Similarity	NPC3403
0.75	Intermediate Similarity	NPC317066
0.75	Intermediate Similarity	NPC139765
0.75	Intermediate Similarity	NPC82955
0.75	Intermediate Similarity	NPC27349
0.75	Intermediate Similarity	NPC102725
0.75	Intermediate Similarity	NPC286719
0.75	Intermediate Similarity	NPC121121
0.75	Intermediate Similarity	NPC24014
0.75	Intermediate Similarity	NPC477286
0.75	Intermediate Similarity	NPC131584
0.75	Intermediate Similarity	NPC475172
0.75	Intermediate Similarity	NPC473472
0.75	Intermediate Similarity	NPC131466
0.7468	Intermediate Similarity	NPC470609
0.7468	Intermediate Similarity	NPC261616
0.7467	Intermediate Similarity	NPC310766
0.7467	Intermediate Similarity	NPC232112
0.7465	Intermediate Similarity	NPC477603
0.7439	Intermediate Similarity	NPC232044
0.7439	Intermediate Similarity	NPC273290
0.7439	Intermediate Similarity	NPC266651
0.7436	Intermediate Similarity	NPC301707
0.7436	Intermediate Similarity	NPC476732
0.7436	Intermediate Similarity	NPC42853
0.7436	Intermediate Similarity	NPC199965

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 NPC99264 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	394
0.1-0.2	4363
0.2-0.3	3133
0.3-0.4	715
0.4-0.5	263
0.5-0.6	213
0.6-0.7	47
0.7-0.8	21
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8824	High Similarity	NPD4267	Clinical (unspecified phase)
0.7671	Intermediate Similarity	NPD4787	Phase 1
0.7568	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD6116	Phase 1
0.7432	Intermediate Similarity	NPD4244	Approved
0.7432	Intermediate Similarity	NPD4789	Approved
0.7432	Intermediate Similarity	NPD4245	Approved
0.7403	Intermediate Similarity	NPD6117	Approved
0.7368	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD3698	Phase 2
0.7297	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD7525	Registered
0.725	Intermediate Similarity	NPD6928	Phase 2
0.7241	Intermediate Similarity	NPD8171	Discontinued
0.7222	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD6114	Approved
0.7215	Intermediate Similarity	NPD6697	Approved
0.7215	Intermediate Similarity	NPD6118	Approved
0.7215	Intermediate Similarity	NPD6115	Approved
0.6933	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD6705	Phase 1
0.6933	Remote Similarity	NPD5360	Phase 3
0.6883	Remote Similarity	NPD6081	Approved
0.6835	Remote Similarity	NPD6942	Approved
0.6835	Remote Similarity	NPD7339	Approved
0.6835	Remote Similarity	NPD3703	Phase 2
0.6824	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.675	Remote Similarity	NPD6933	Approved
0.6742	Remote Similarity	NPD8035	Phase 2
0.6742	Remote Similarity	NPD8034	Phase 2
0.6707	Remote Similarity	NPD7645	Phase 2
0.6667	Remote Similarity	NPD4224	Phase 2
0.6585	Remote Similarity	NPD3671	Phase 1
0.6543	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.65	Remote Similarity	NPD6926	Approved
0.65	Remote Similarity	NPD6924	Approved
0.6495	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6456	Remote Similarity	NPD4758	Discontinued
0.6456	Remote Similarity	NPD5777	Approved
0.642	Remote Similarity	NPD3702	Approved
0.6395	Remote Similarity	NPD4788	Approved
0.6386	Remote Similarity	NPD5364	Discontinued
0.6344	Remote Similarity	NPD7991	Discontinued
0.6322	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6322	Remote Similarity	NPD4786	Approved
0.631	Remote Similarity	NPD6929	Approved
0.6292	Remote Similarity	NPD7524	Approved
0.6264	Remote Similarity	NPD6701	Clinical (unspecified phase)
0.6264	Remote Similarity	NPD6700	Approved
0.625	Remote Similarity	NPD4243	Approved
0.6235	Remote Similarity	NPD6931	Approved
0.6235	Remote Similarity	NPD4748	Discontinued
0.6235	Remote Similarity	NPD6930	Phase 2
0.6212	Remote Similarity	NPD384	Approved
0.6212	Remote Similarity	NPD385	Approved
0.6207	Remote Similarity	NPD6695	Phase 3
0.6203	Remote Similarity	NPD6922	Approved
0.6203	Remote Similarity	NPD6923	Approved
0.6196	Remote Similarity	NPD6703	Approved
0.6196	Remote Similarity	NPD6702	Approved
0.6184	Remote Similarity	NPD371	Approved
0.6139	Remote Similarity	NPD8174	Phase 2
0.6125	Remote Similarity	NPD7144	Approved
0.6125	Remote Similarity	NPD7143	Approved
0.6111	Remote Similarity	NPD7750	Discontinued
0.6098	Remote Similarity	NPD4785	Approved
0.6098	Remote Similarity	NPD4784	Approved
0.6092	Remote Similarity	NPD3667	Approved
0.6071	Remote Similarity	NPD5776	Phase 2
0.6071	Remote Similarity	NPD6932	Approved
0.6071	Remote Similarity	NPD6925	Approved
0.6049	Remote Similarity	NPD7151	Approved
0.6049	Remote Similarity	NPD7152	Approved
0.6049	Remote Similarity	NPD7150	Approved
0.6047	Remote Similarity	NPD7509	Discontinued
0.6042	Remote Similarity	NPD7920	Phase 3
0.6042	Remote Similarity	NPD7919	Phase 3
0.6	Remote Similarity	NPD7145	Approved
0.5979	Remote Similarity	NPD8088	Phase 1
0.5978	Remote Similarity	NPD4753	Phase 2
0.5978	Remote Similarity	NPD5328	Approved
0.5957	Remote Similarity	NPD6399	Phase 3
0.5955	Remote Similarity	NPD3666	Approved
0.5955	Remote Similarity	NPD3133	Approved
0.5955	Remote Similarity	NPD3665	Phase 1
0.5934	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.593	Remote Similarity	NPD6683	Phase 2
0.5918	Remote Similarity	NPD8418	Phase 2
0.5889	Remote Similarity	NPD6893	Approved
0.5882	Remote Similarity	NPD6412	Phase 2
0.5876	Remote Similarity	NPD4755	Approved
0.5862	Remote Similarity	NPD7514	Phase 3
0.5851	Remote Similarity	NPD6079	Approved
0.5851	Remote Similarity	NPD7515	Phase 2
0.5849	Remote Similarity	NPD8133	Approved
0.5833	Remote Similarity	NPD4190	Phase 3
0.5833	Remote Similarity	NPD5275	Approved
0.5824	Remote Similarity	NPD3618	Phase 1
0.5824	Remote Similarity	NPD8308	Discontinued
0.5795	Remote Similarity	NPD6902	Approved
0.5789	Remote Similarity	NPD4202	Approved
0.5758	Remote Similarity	NPD4700	Approved
0.5758	Remote Similarity	NPD4696	Approved
0.5758	Remote Similarity	NPD5286	Approved
0.5758	Remote Similarity	NPD5285	Approved
0.5747	Remote Similarity	NPD4195	Approved
0.5741	Remote Similarity	NPD6940	Discontinued
0.5729	Remote Similarity	NPD7748	Approved
0.5714	Remote Similarity	NPD1810	Approved
0.5714	Remote Similarity	NPD6083	Phase 2
0.5714	Remote Similarity	NPD6084	Phase 2
0.5714	Remote Similarity	NPD1811	Approved
0.5714	Remote Similarity	NPD7902	Approved
0.5684	Remote Similarity	NPD7087	Discontinued
0.5682	Remote Similarity	NPD7332	Phase 2
0.5676	Remote Similarity	NPD8377	Approved
0.5676	Remote Similarity	NPD8294	Approved
0.567	Remote Similarity	NPD4629	Approved
0.567	Remote Similarity	NPD5210	Approved
0.5658	Remote Similarity	NPD3198	Approved
0.5657	Remote Similarity	NPD7638	Approved
0.5652	Remote Similarity	NPD5279	Phase 3
0.5644	Remote Similarity	NPD5225	Approved
0.5644	Remote Similarity	NPD5224	Approved
0.5644	Remote Similarity	NPD5211	Phase 2
0.5644	Remote Similarity	NPD5226	Approved
0.5644	Remote Similarity	NPD4633	Approved
0.5636	Remote Similarity	NPD7327	Approved
0.5636	Remote Similarity	NPD7328	Approved
0.5632	Remote Similarity	NPD3617	Approved
0.5632	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.5631	Remote Similarity	NPD6675	Approved
0.5631	Remote Similarity	NPD5739	Approved
0.5631	Remote Similarity	NPD7128	Approved
0.5631	Remote Similarity	NPD6920	Discontinued
0.5631	Remote Similarity	NPD6402	Approved
0.5625	Remote Similarity	NPD8033	Approved
0.5625	Remote Similarity	NPD8380	Approved
0.5625	Remote Similarity	NPD8296	Approved
0.5625	Remote Similarity	NPD8379	Approved
0.5625	Remote Similarity	NPD8335	Approved
0.5625	Remote Similarity	NPD8378	Approved
0.5618	Remote Similarity	NPD6898	Phase 1
0.5612	Remote Similarity	NPD4697	Phase 3
0.5612	Remote Similarity	NPD5222	Approved
0.5612	Remote Similarity	NPD5221	Approved
0.5612	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5607	Remote Similarity	NPD8297	Approved
0.5604	Remote Similarity	NPD3668	Phase 3
0.56	Remote Similarity	NPD7640	Approved
0.56	Remote Similarity	NPD7639	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