NPASS Compound

Natural Product: NPC479940

Natural Product ID	NPC479940
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	RPWVYPXPSCDKKD-VWQWQMIBSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds]

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 79 81 0 0 0 0 0 0 0 0999 V2000 -3.1417 -5.0742 -3.5177 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2329 -4.3011 -4.0188 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6531 -3.1486 -3.3833 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7448 -2.4403 -3.9791 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0693 -2.7256 -1.9800 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2906 -1.5461 -1.5381 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5779 -1.0125 -0.1487 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3141 -2.2856 0.6995 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9349 -0.5470 0.1106 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8095 -0.2611 -1.1044 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1143 0.5930 1.0483 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9431 1.4151 1.4208 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9135 1.4171 0.3250 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2860 2.2074 0.8651 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3138 1.6621 1.4473 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5050 0.2139 1.6814 C 0 0 1 0 0 0 0 0 0 0 0 0 0.2696 -0.5283 1.3204 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4796 0.0174 0.0824 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6585 -0.3133 1.0023 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6746 -0.9189 1.7589 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4711 -0.9474 3.0100 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8894 -1.4802 1.1208 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7372 -2.1230 2.1960 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9746 -3.2240 2.8932 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1997 -1.0834 3.1897 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0303 3.6021 0.4759 C 0 0 1 0 0 0 0 0 0 0 0 0 1.1072 4.4563 0.4854 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1219 5.6919 1.1071 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0806 6.0798 1.6934 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3228 6.5668 1.1011 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3294 3.3646 -0.8757 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3179 2.3097 -0.7480 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.4613 1.8718 -2.0505 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5517 2.3717 -2.7861 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3431 3.1854 -2.2650 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7978 1.9531 -4.1957 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4237 2.7218 1.7051 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5910 -4.9454 -2.5291 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5538 -5.9474 -4.0472 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8761 -4.5559 -5.0286 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2853 -1.5912 -3.5708 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3980 -2.7403 -4.9852 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8921 -3.6366 -1.3709 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1455 -2.5640 -2.0363 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3251 -0.7077 -2.2850 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2103 -1.8401 -1.5259 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3365 -2.1187 1.7592 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2779 -2.8783 0.5000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5476 -2.9291 0.2716 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5043 -1.4046 0.6057 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2655 0.7766 -1.0376 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6868 -0.9253 -1.1949 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2854 -0.2629 -2.0538 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9226 1.3039 0.6802 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5723 0.2704 2.0423 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5043 1.1232 2.4256 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0952 2.3820 1.7827 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6431 0.0807 2.7981 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5996 -1.5461 1.0407 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3887 -0.5021 2.2248 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2771 0.0361 -0.7119 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4273 -0.6306 0.6406 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5934 -2.2602 0.3918 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6085 -2.6111 1.6895 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5618 -4.1466 2.8960 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0166 -3.3955 2.3510 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7561 -2.9841 3.9613 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3584 -0.1375 2.6694 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1703 -1.4849 3.6197 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4975 -1.0148 4.0612 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7890 4.1185 1.0333 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1118 7.5357 1.6278 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1352 6.1033 1.6894 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6517 6.8677 0.0915 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1986 2.9773 -0.4253 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3858 2.7328 -4.8677 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4033 0.9365 -4.4108 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9162 1.9736 -4.3357 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3793 2.8024 1.5482 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 0 3 4 2 0 3 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 7 9 1 0 9 10 1 0 9 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 2 0 15 16 1 0 16 17 1 0 17 18 1 0 16 19 1 0 19 20 1 0 20 21 2 0 20 22 1 0 22 23 1 0 23 24 1 0 23 25 1 0 14 26 1 0 26 27 1 0 27 28 1 0 28 29 2 0 28 30 1 0 26 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 34 35 2 0 34 36 1 0 12 37 1 0 18 7 1 0 18 13 1 0 32 13 1 0 1 38 1 0 1 39 1 0 2 40 1 0 4 41 1 0 4 42 1 0 5 43 1 0 5 44 1 0 6 45 1 0 6 46 1 0 8 47 1 0 8 48 1 0 8 49 1 0 9 50 1 0 10 51 1 0 10 52 1 0 10 53 1 0 11 54 1 0 11 55 1 0 12 56 1 0 15 57 1 0 16 58 1 1 17 59 1 0 17 60 1 0 18 61 1 0 22 62 1 0 22 63 1 0 23 64 1 0 24 65 1 0 24 66 1 0 24 67 1 0 25 68 1 0 25 69 1 0 25 70 1 0 26 71 1 1 30 72 1 0 30 73 1 0 30 74 1 0 32 75 1 1 36 76 1 0 36 77 1 0 36 78 1 0 37 79 1 0 M END

Standard InCHIKey	RPWVYPXPSCDKKD-VWQWQMIBSA-N
Standard InCHI	InChI=1S/C29H42O8/c1-9-17(4)10-11-28(8)18(5)13-24(32)29-22(26(34-19(6)30)37-27(29)35-20(7)31)14-21(15-23(28)29)36-25(33)12-16(2)3/h9,14,16,18,21,23-24,26-27,32H,1,4,10-13,15H2,2-3,5-8H3/t18?,21-,23?,24?,26-,27+,28?,29?/m0/s1
SMILES	C=CC(=C)CCC1(C)C(C)CC(C23C(=C[C@@H](CC12)OC(=O)CC(C)C)[C@@H](OC(=O)C)O[C@H]3OC(=O)C)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	518.29	Volume:	538.974 ? Van der Waals volume.
Dense:	0.962	LogP:	3.707 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.671 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.492 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	12.0	Rigid Bonds:	20.0
TPSA:	108.36 ? Topological Polar Surface Area.	H-Bond Acceptor:	8.0
H-Bond Donor:	1.0	Rings:	3.0
Heavy Atoms:	8.0

MedChem Properties

QED Drug-Likeness Score:	0.204	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.739	Fsp³:	0.69
MCE-18:	92.02 ? 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:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.398	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.005 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.133 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.17	Promiscuous compounds:	0.165

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.822	MDCK Permeability:	-4.729
Pgp-inhibitor:	0.159	Pgp-substrate:	0.675
PAMPA:	0.496 ? 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):	0.014
20% Bioavailability (F20%):	0.975	30% Bioavailability (F30%):	0.994
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.287	MRP1:	0.977
Plasma Protein Binding (PPB):	70.866%	Volume Distribution (VD):	0.003
Fu:	27.169% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.99
OATP1B3 inhibitor:	0.967	BCRP inhibitor:	0.294
BSEP inhibitor:	0.989

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.986
CYP2C19-inhibitor:	0.805	CYP2C19-substrate:	0.187
CYP2C9-inhibitor:	0.006	CYP2C9-substrate:	0.001
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.006
CYP3A4-inhibitor:	0.015	CYP3A4-substrate:	0.007
CYP2B6-substrate:	0.001	CYP2C8-inhibitor:	0.993
HLM stability:	0.999 ? 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):

7.931

Half-life (T1/2):

1.123

ADMET: Toxicity

hERG Blockers:	0.054	hERG Blockers (10um):	0.367
Human Hepatotoxicity (H-HT):	0.632	Drug-induced Liver Injury (DILI):	0.784
AMES Toxicity:	0.977	Rat Oral Acute Toxicity:	0.865
Maximum Recommended Daily Dose:	0.985	Skin Sensitization:	0.988
Carcinogencity:	0.557	Eye Corrosion:	0.0
Eye Irritation:	0.003	Respiratory Toxicity:	0.24
Drug-induced Neurotoxicity:	0.869	Ototoxicity:	0.739
Hematotoxicity:	0.238	Drug-induced Nephrotoxicity:	0.908
Genotoxicity:	0.997	RPMI-8226 Immunitoxicity:	0.406
A549 Cytotoxicity:	0.665	Hek293 Cytotoxicity:	0.523
BCF:	0.922 ? 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:	3.911 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.956 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.103 ? 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
NPO40015	Anacolosa clarkii	Species	Aptandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30830773]

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
TGI	4

Activity Type	# Activity
Cell line	2
Others	2

Molecular-level activity

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

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2276	Cell line	A673	Homo sapiens	TGI	=	700.0	nM	PMID[30830773]
NPT15166	Cell line	Hep293TT	Homo sapiens	TGI	=	220.0	nM	PMID[30830773]
NPT2	Others	Unspecified	n.a.	TGI	=	340.0	nM	PMID[30830773]
NPT2	Others	Unspecified	n.a.	TGI	=	360.0	nM	PMID[30830773]

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 NPC479940 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	18557
0.1-0.2	26762
0.2-0.3	4375
0.3-0.4	42
0.4-0.5	38
0.5-0.6	36
0.6-0.7	30
0.7-0.8	0
0.8-0.85	1
0.85-0.9	3
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.931	High Similarity	NPC479943
0.9	High Similarity	NPC7644
0.8548	High Similarity	NPC475889
0.8548	High Similarity	NPC7613
0.8548	High Similarity	NPC479942
0.8413	Intermediate Similarity	NPC479941
0.7969	Intermediate Similarity	NPC238397
0.7812	Intermediate Similarity	NPC479497
0.7812	Intermediate Similarity	NPC81567
0.7812	Intermediate Similarity	NPC488652
0.7761	Intermediate Similarity	NPC127933
0.7727	Intermediate Similarity	NPC471363
0.7538	Intermediate Similarity	NPC128795
0.7273	Intermediate Similarity	NPC488654
0.7273	Intermediate Similarity	NPC479491
0.726	Intermediate Similarity	NPC486751
0.7077	Intermediate Similarity	NPC602188
0.7015	Intermediate Similarity	NPC201880
0.6986	Remote Similarity	NPC87630
0.6912	Remote Similarity	NPC217921
0.6912	Remote Similarity	NPC88013
0.6912	Remote Similarity	NPC135015
0.6765	Remote Similarity	NPC329623
0.6765	Remote Similarity	NPC609711
0.6716	Remote Similarity	NPC488653
0.6714	Remote Similarity	NPC488964
0.6714	Remote Similarity	NPC184512
0.6667	Remote Similarity	NPC330003
0.6667	Remote Similarity	NPC470321
0.6667	Remote Similarity	NPC264867
0.6667	Remote Similarity	NPC473207
0.6667	Remote Similarity	NPC609715
0.6567	Remote Similarity	NPC479936
0.6567	Remote Similarity	NPC318917
0.6567	Remote Similarity	NPC488659
0.6567	Remote Similarity	NPC604149
0.6533	Remote Similarity	NPC179128
0.6522	Remote Similarity	NPC134270
0.6286	Remote Similarity	NPC488660
0.6286	Remote Similarity	NPC488657
0.6286	Remote Similarity	NPC609880
0.625	Remote Similarity	NPC252296
0.6197	Remote Similarity	NPC488658
0.6197	Remote Similarity	NPC488655
0.6176	Remote Similarity	NPC479934
0.6056	Remote Similarity	NPC311223
0.6056	Remote Similarity	NPC316974
0.6029	Remote Similarity	NPC171598
0.5946	Remote Similarity	NPC125423
0.589	Remote Similarity	NPC48548
0.5867	Remote Similarity	NPC40728
0.5857	Remote Similarity	NPC479935
0.5857	Remote Similarity	NPC481019
0.5797	Remote Similarity	NPC481018
0.5775	Remote Similarity	NPC488656
0.5775	Remote Similarity	NPC488236
0.575	Remote Similarity	NPC109376
0.5732	Remote Similarity	NPC224660
0.5694	Remote Similarity	NPC471366
0.5694	Remote Similarity	NPC476800
0.5694	Remote Similarity	NPC488237
0.5652	Remote Similarity	NPC472189
0.5647	Remote Similarity	NPC481025
0.5634	Remote Similarity	NPC479939
0.5616	Remote Similarity	NPC481017
0.5588	Remote Similarity	NPC476802
0.5556	Remote Similarity	NPC472186
0.5556	Remote Similarity	NPC479937
0.5541	Remote Similarity	NPC473545
0.55	Remote Similarity	NPC116292
0.5493	Remote Similarity	NPC481020
0.5479	Remote Similarity	NPC488649
0.5479	Remote Similarity	NPC479938
0.5417	Remote Similarity	NPC471362
0.5417	Remote Similarity	NPC471372
0.5342	Remote Similarity	NPC472188
0.5325	Remote Similarity	NPC488221
0.5325	Remote Similarity	NPC488220
0.5325	Remote Similarity	NPC488216
0.5286	Remote Similarity	NPC89171
0.5278	Remote Similarity	NPC488651
0.5278	Remote Similarity	NPC488648
0.5195	Remote Similarity	NPC472187
0.5062	Remote Similarity	NPC486752

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC479940 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6941
0.1-0.2	2141
0.2-0.3	68
0.3-0.4	0
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