NPASS Compound

Natural Product: NPC207922

Natural Product ID	NPC207922
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	(1R,2R,4As,6Ar,6As,6Br,8Ar,10R,11S,12Ar,14Bs)-1,10,11-Trihydroxy-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
IUPAC Name	(1R,2R,4aS,6aR,6aS,6bR,8aR,10R,11S,12aR,14bS)-1,10,11-trihydroxy-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
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1270647
PubChem CID	490364
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

The Chemical Classification was calculated by Classyfire, a software for chemical taxonomy calculation. Reference: DOI:10.1186/s13321-016-0174-y.

Chemical Representations

RDKit 3D 83 87 0 0 0 0 0 0 0 0999 V2000 -5.8389 2.4869 0.9854 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1681 1.3611 0.2452 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.8715 0.0582 0.3413 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0286 -1.0985 0.7296 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6846 -1.1583 0.0197 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.8267 -2.0646 0.8524 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4595 -2.1497 0.2754 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7962 -0.7928 0.3537 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5377 -0.4870 1.7814 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6432 0.2395 -0.3522 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1062 1.2171 -1.0759 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3410 1.4201 -1.2811 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1307 0.4585 -0.4560 C 0 0 2 0 0 0 0 0 0 0 0 0 2.6125 0.4830 -0.7298 C 0 0 1 0 0 0 0 0 0 0 0 0 2.9875 0.1892 -2.1362 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0405 1.9097 -0.4235 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4853 2.0977 -0.1894 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1768 1.0593 0.6054 C 0 0 1 0 0 0 0 0 0 0 0 0 4.7183 -0.3416 0.4078 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5255 -0.9875 -0.6735 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0747 -1.0863 1.7105 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2446 -0.4577 0.2565 C 0 0 2 0 0 0 0 0 0 0 0 0 2.7838 -1.8484 -0.0238 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2971 -1.9923 0.1307 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4967 -0.8863 -0.4730 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0626 -1.2001 -1.8946 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5487 1.1016 0.2623 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1481 2.3730 -1.4101 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1176 0.1864 -0.2627 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.7135 1.1908 0.6978 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.0184 2.5170 0.6989 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7361 0.7419 2.0174 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9119 -1.8630 -1.2918 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7082 -1.3117 -2.4013 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3610 -3.1641 -1.2883 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.6872 2.4737 2.0635 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3745 3.4379 0.5903 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8884 2.5140 0.6727 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1084 1.6538 -0.8241 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6761 0.1606 1.1111 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4311 -0.1737 -0.6112 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9209 -1.2470 1.8324 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5806 -2.0309 0.4047 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8513 -1.6712 1.8806 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3506 -3.0492 0.8882 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8430 -2.8283 0.9257 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4649 -2.5765 -0.7256 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0130 0.5059 2.0210 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9899 -1.2015 2.5117 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5362 -0.4663 2.0699 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7608 1.9531 -1.5794 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5654 2.4619 -0.9022 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5607 1.4392 -2.3465 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0431 0.8440 0.6070 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9321 -0.8532 -2.4487 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4604 0.8825 -2.8202 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0755 0.4777 -2.2478 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7029 2.5329 -1.2692 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4650 2.2646 0.4672 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5950 3.0702 0.3840 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1636 1.3317 1.7016 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9576 -1.5818 -1.3912 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3213 -1.6835 -0.2704 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1309 -0.2046 -1.2197 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1262 -2.1672 1.5336 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3712 -0.7900 2.5029 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0807 -0.7077 2.0245 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8000 -0.1780 1.2611 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2674 -2.5101 0.7542 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0798 -2.2607 -0.9854 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0196 -2.9501 -0.4042 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0794 -2.2099 1.1928 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2343 -2.2843 -2.1149 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5634 -0.5738 -2.6498 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0241 -1.0433 -2.0427 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9561 1.9503 0.5375 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1059 2.2062 -1.3249 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5152 0.4936 -1.2812 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2708 3.1587 -0.1737 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4520 3.0809 1.5748 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9552 2.3963 0.8971 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3343 1.3652 2.6507 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8479 -3.6129 -2.0559 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 1 8 10 1 0 10 11 2 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 6 14 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 19 21 1 0 19 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 6 18 27 1 0 17 28 1 0 10 29 1 0 29 30 1 0 30 31 1 0 30 32 1 1 5 33 1 6 33 34 2 0 33 35 1 0 30 2 1 0 29 5 1 0 25 8 1 0 25 13 1 0 22 14 1 0 1 36 1 0 1 37 1 0 1 38 1 0 2 39 1 6 3 40 1 0 3 41 1 0 4 42 1 0 4 43 1 0 6 44 1 0 6 45 1 0 7 46 1 0 7 47 1 0 9 48 1 0 9 49 1 0 9 50 1 0 11 51 1 0 12 52 1 0 12 53 1 0 13 54 1 1 15 55 1 0 15 56 1 0 15 57 1 0 16 58 1 0 16 59 1 0 17 60 1 1 18 61 1 1 20 62 1 0 20 63 1 0 20 64 1 0 21 65 1 0 21 66 1 0 21 67 1 0 22 68 1 1 23 69 1 0 23 70 1 0 24 71 1 0 24 72 1 0 26 73 1 0 26 74 1 0 26 75 1 0 27 76 1 0 28 77 1 0 29 78 1 6 31 79 1 0 31 80 1 0 31 81 1 0 32 82 1 0 35 83 1 0 M END

Standard InCHIKey	OXVUXGFZHDKYLS-VCFAZYFWSA-N
Standard InCHI	InChI=1S/C30H48O5/c1-17-10-13-30(24(33)34)15-14-27(5)18(22(30)29(17,7)35)8-9-21-26(4)16-19(31)23(32)25(2,3)20(26)11-12-28(21,27)6/h8,17,19-23,31-32,35H,9-16H2,1-7H3,(H,33,34)/t17-,19+,20+,21-,22-,23+,26+,27-,28-,29-,30+/m1/s1
SMILES	C[C@@H]1CC[C@@]2(CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)C[C@@H]([C@@H](C(C)(C)[C@@H]5CC[C@@]34C)O)O)[C@@H]2[C@]1(C)O)C(=O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	488.35	Volume:	523.332 ? Van der Waals volume.
Dense:	0.933	LogP:	2.757 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.764 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.684 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	1.0	Rigid Bonds:	27.0
TPSA:	97.99 ? Topological Polar Surface Area.	H-Bond Acceptor:	5.0
H-Bond Donor:	4.0	Rings:	5.0
Heavy Atoms:	5.0

MedChem Properties

QED Drug-Likeness Score:	0.382	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.044	Fsp³:	0.9
MCE-18:	110.772 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.648	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.052 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.0 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.308	Promiscuous compounds:	0.075

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.607	MDCK Permeability:	-5.13
Pgp-inhibitor:	0.0	Pgp-substrate:	0.04
PAMPA:	1.0 ? The experimental data for Peff was logarithmically transformed (logPeff). Molecules with log Peff values below 2.0 were classified as low-permeability (Category 0), while those with log Peff values exceeding 2.5 were classified as high-permeability (Category 1).	Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.451	30% Bioavailability (F30%):	0.104
50% Bioavailability (F50%):	0.97

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.044	MRP1:	0.997
Plasma Protein Binding (PPB):	88.456%	Volume Distribution (VD):	-0.369
Fu:	10.187% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.948	BCRP inhibitor:	0.0
BSEP inhibitor:	0.552

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.162	CYP2C19-substrate:	0.002
CYP2C9-inhibitor:	0.805	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.034	CYP3A4-substrate:	0.033
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.034
HLM stability:	0.004 ? Human liver microsomal (HLM) stability. Category 0: stable+ (HLM > 30 min); Category 1: unstable- (HLM ≤ 30 min). The output value is the probability of human liver microsomal instability, where a value closer to 1 indicates a higher likelihood of instability.

ADMET: Excretion

Clearance (CL):

2.998

Half-life (T1/2):

1.357

ADMET: Toxicity

hERG Blockers:	0.019	hERG Blockers (10um):	0.05
Human Hepatotoxicity (H-HT):	0.665	Drug-induced Liver Injury (DILI):	0.52
AMES Toxicity:	0.431	Rat Oral Acute Toxicity:	0.447
Maximum Recommended Daily Dose:	0.318	Skin Sensitization:	0.974
Carcinogencity:	0.879	Eye Corrosion:	0.017
Eye Irritation:	0.539	Respiratory Toxicity:	0.924
Drug-induced Neurotoxicity:	0.092	Ototoxicity:	0.68
Hematotoxicity:	0.596	Drug-induced Nephrotoxicity:	0.954
Genotoxicity:	0.897	RPMI-8226 Immunitoxicity:	0.048
A549 Cytotoxicity:	0.444	Hek293 Cytotoxicity:	0.214
BCF:	1.001 ? Bioconcentration factors are used for considering secondary poisoning potential and assessing risks to human health via the food chain. The unit is -log10[(mg/L)/(1000*MW)].	IGC50:	3.498 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.005 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.331 ? 96 hour fathead minnow LC50. The unit of LC50FM is -log10[(mg/L)/(1000*MW)].

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO3595	Euscaphis japonica	Species	Staphyleaceae	Eukaryota	n.a.	twig	n.a.	DOI[10.1021/np1003593]
NPO3595	Euscaphis japonica	Species	Staphyleaceae	Eukaryota	Twigs	Yangming mountain, Taiwan	2008-APR	PMID[20873721]
NPO3595	Euscaphis japonica	Species	Staphyleaceae	Eukaryota	n.a.	pericarp	n.a.	PMID[4421158]
NPO3595	Euscaphis japonica	Species	Staphyleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3595	Euscaphis japonica	Species	Staphyleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3595	Euscaphis japonica	Species	Staphyleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3595	Euscaphis japonica	Species	Staphyleaceae	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	Organism Name	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
Inhibition	1
Activity	4

Activity Type	# Activity
Individual protein	1
Cell line	4

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT5212	Individual protein	Sentrin-specific protease 1	Homo sapiens	Inhibition	=	1.7	%	PMID[35500202]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell line	MCF7	Homo sapiens	Activity	=	70.0	%	PMID[20873721]
NPT397	Cell line	NCI-H460	Homo sapiens	Activity	=	78.0	%	PMID[20873721]
NPT139	Cell line	HT-29	Homo sapiens	Activity	=	74.0	%	PMID[20873721]
NPT404	Cell line	CCRF-CEM	Homo sapiens	Activity	=	73.0	%	PMID[20873721]

In vivo activity

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

Experimental ADME

Experiment Model	Experiment Tissue	ADME Type	ADME Relation	ADME Value	ADME Unit	Reference

Experimental Toxicity

Quantitative toxicity

Experiment Model	Experiment Organism	Toxicity Type	Toxicity Relation	Toxicity Value	Toxicity Unit	Reference

Common Abbreviations:
LC: Lethal Concentration; LD: Lethal Dose; LT:Lethal Time; NOAEL: No-observed-adverse-effect Level; BMDL: Benchmark Dose Lower Confidence Limit; BMD: Benchmark Dose; BMC:Benchmark Concentration; LOAEL: Lowest Observed Adverse Effect Level; RfD:Reference Dose; RfC:Reference Concentration; MRL: Minimal Risk Level; MEG: Maximum Exposure Guideline; PAC: Protective Action Criteria

Categorical toxicity labels

Hepatotoxicity	Carcinogenicity	Mutagenicity	Cardiotoxicity	Respiratory Toxicity	Eye Irritation	Endocrine Disruption

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 toxicity records from domain-specific databases. These databases include:
☉ ToxValDB: a curated database that compiles quantitative toxicity values for chemicals from diverse public sources to support toxicological research and risk assessment.
☉ TOXRIC: a comprehensive, free-to-access, online database providing toxicological/feature data. The toxicity labels are retrieved from this database. [PMID: 36400569]

Chemically structural similarity

Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes approximately 50,000 NPs with experimentally-derived bioactivity available in NPASS)

Similarity is measured using the Tanimoto coefficient (Tc) , which compares the binary fingerprints of two molecules. Tc is calculated as the intersection divided by the union of '1' bits in the fingerprints, ranging from 0 to 1, with 1 indicating highest similarity.

● The left chart: Distribution of similarity level between NPC207922 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	24624
0.1-0.2	21730
0.2-0.3	2832
0.3-0.4	418
0.4-0.5	138
0.5-0.6	54
0.6-0.7	25
0.7-0.8	0
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC259733
1.0	High Similarity	NPC158371
0.8571	High Similarity	NPC247139
0.7846	Intermediate Similarity	NPC202728
0.7846	Intermediate Similarity	NPC158059
0.7826	Intermediate Similarity	NPC96693
0.7576	Intermediate Similarity	NPC256247
0.75	Intermediate Similarity	NPC157113
0.7463	Intermediate Similarity	NPC35239
0.7424	Intermediate Similarity	NPC71074
0.7424	Intermediate Similarity	NPC37221
0.7424	Intermediate Similarity	NPC605937
0.7353	Intermediate Similarity	NPC62516
0.7313	Intermediate Similarity	NPC136697
0.7273	Intermediate Similarity	NPC84319
0.7273	Intermediate Similarity	NPC52021
0.7273	Intermediate Similarity	NPC599947
0.7206	Intermediate Similarity	NPC191412
0.7206	Intermediate Similarity	NPC114159
0.7206	Intermediate Similarity	NPC132824
0.7206	Intermediate Similarity	NPC6818
0.7164	Intermediate Similarity	NPC472149
0.7083	Intermediate Similarity	NPC54909
0.7	Intermediate Similarity	NPC187933
0.7	Intermediate Similarity	NPC284865
0.6857	Remote Similarity	NPC118964
0.6857	Remote Similarity	NPC25299
0.6857	Remote Similarity	NPC481322
0.6857	Remote Similarity	NPC148964
0.6849	Remote Similarity	NPC233012
0.6714	Remote Similarity	NPC118519
0.6667	Remote Similarity	NPC235053
0.6575	Remote Similarity	NPC603658
0.6479	Remote Similarity	NPC9613
0.6429	Remote Similarity	NPC88116
0.6389	Remote Similarity	NPC137072
0.6338	Remote Similarity	NPC32407
0.6338	Remote Similarity	NPC263548
0.6338	Remote Similarity	NPC606320
0.6301	Remote Similarity	NPC147232
0.6207	Remote Similarity	NPC482049
0.6207	Remote Similarity	NPC482050
0.6197	Remote Similarity	NPC231063
0.6197	Remote Similarity	NPC282395
0.6197	Remote Similarity	NPC173744
0.6197	Remote Similarity	NPC204961
0.6197	Remote Similarity	NPC73004
0.6197	Remote Similarity	NPC110308
0.6197	Remote Similarity	NPC609452
0.6056	Remote Similarity	NPC306541
0.5974	Remote Similarity	NPC327179
0.5915	Remote Similarity	NPC96916
0.5867	Remote Similarity	NPC20235
0.5867	Remote Similarity	NPC299996
0.5775	Remote Similarity	NPC43686
0.5753	Remote Similarity	NPC300351
0.575	Remote Similarity	NPC600756
0.5658	Remote Similarity	NPC116457
0.5658	Remote Similarity	NPC174663
0.5616	Remote Similarity	NPC51700
0.5616	Remote Similarity	NPC259788
0.5616	Remote Similarity	NPC88716
0.5616	Remote Similarity	NPC255589
0.5616	Remote Similarity	NPC68160
0.5584	Remote Similarity	NPC479743
0.557	Remote Similarity	NPC188833
0.5556	Remote Similarity	NPC25491
0.5556	Remote Similarity	NPC609710
0.5541	Remote Similarity	NPC481360
0.5526	Remote Similarity	NPC203343
0.5526	Remote Similarity	NPC312075
0.5479	Remote Similarity	NPC480946
0.5479	Remote Similarity	NPC187722
0.5479	Remote Similarity	NPC130577
0.5479	Remote Similarity	NPC142415
0.5479	Remote Similarity	NPC102683
0.5467	Remote Similarity	NPC305464
0.5467	Remote Similarity	NPC87095
0.5467	Remote Similarity	NPC19376
0.5467	Remote Similarity	NPC293564
0.5467	Remote Similarity	NPC25848
0.5444	Remote Similarity	NPC488214
0.5435	Remote Similarity	NPC482051
0.5405	Remote Similarity	NPC182797
0.5405	Remote Similarity	NPC52169
0.5405	Remote Similarity	NPC488562
0.5395	Remote Similarity	NPC201657
0.5333	Remote Similarity	NPC106112
0.5333	Remote Similarity	NPC261935
0.5333	Remote Similarity	NPC111214
0.5275	Remote Similarity	NPC482052
0.5263	Remote Similarity	NPC145667
0.5205	Remote Similarity	NPC488506
0.5205	Remote Similarity	NPC220498
0.52	Remote Similarity	NPC307282
0.5195	Remote Similarity	NPC88847
0.5155	Remote Similarity	NPC481234
0.5155	Remote Similarity	NPC479431
0.5132	Remote Similarity	NPC61543
0.5132	Remote Similarity	NPC293048
0.5132	Remote Similarity	NPC225585
0.5067	Remote Similarity	NPC136313
0.5065	Remote Similarity	NPC477288
0.5062	Remote Similarity	NPC230151

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC207922 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6725
0.1-0.2	2365
0.2-0.3	56
0.3-0.4	4
0.4-0.5	0
0.5-0.6	0
0.6-0.7	0
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
		NPD

Bioactivity similarity

Similar Natural Products in NPASS

Similarity level is defined by 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