NPASS Compound

Natural Product: NPC603388

Natural Product ID	NPC603388
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	BVJDDPRBYGBPKD-TVZSAIOCSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL522595
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 81 86 0 0 0 0 0 0 0 0999 V2000 -6.1600 1.5329 -1.4078 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1659 0.9583 -0.4334 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8637 2.0295 0.5937 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7814 -0.2181 0.2372 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8097 -1.0238 1.0756 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5749 -1.2409 0.2386 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6836 -2.3150 0.6934 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3506 -1.9424 1.2093 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7355 -0.7014 0.6520 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8018 0.3438 1.7547 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5478 -0.1888 -0.4964 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9760 1.0166 -1.1709 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4176 0.6042 -1.6721 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1945 0.2945 -0.4293 C 0 0 2 0 0 0 0 0 0 0 0 0 2.6667 0.3984 -0.7059 C 0 0 1 0 0 0 0 0 0 0 0 0 3.0671 -0.2457 -2.0034 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9517 1.8937 -0.8799 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8597 2.4185 0.2106 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1447 1.6093 0.2551 C 0 0 2 0 0 0 0 0 0 0 0 0 5.8295 1.7604 -0.9442 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8735 0.1494 0.5138 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6844 -0.7341 -0.3516 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3156 -0.1046 1.9660 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4000 -0.0721 0.4872 C 0 0 2 0 0 0 0 0 0 0 0 0 2.9963 -1.5032 0.7702 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5758 -1.3908 1.3650 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7146 -0.9534 0.2021 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6523 -2.1367 -0.7391 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9425 0.0931 -0.0058 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.8454 0.6297 -1.1236 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.9533 -0.4753 -1.9670 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0756 -1.5858 -1.1436 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5272 -2.7007 -1.4812 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9752 2.0021 -0.7883 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6845 2.3714 -1.9691 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5762 0.7733 -2.1010 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7619 1.6092 1.6117 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7058 2.7795 0.6474 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9738 2.6327 0.3032 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3394 -0.8661 -0.4721 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5495 0.1716 0.9558 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5901 -0.5250 2.0313 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2803 -2.0081 1.2750 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2411 -2.9018 1.4873 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5290 -3.0985 -0.1099 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4129 -1.9133 2.3398 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6179 -2.7871 1.0343 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7455 1.3742 1.3762 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0882 0.1573 2.5835 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7965 0.1772 2.2728 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6868 -0.9546 -1.3087 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5650 1.1535 -2.1262 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9492 1.9258 -0.5735 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8619 1.4056 -2.2852 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2345 -0.2651 -2.3309 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9650 1.1346 0.2939 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2258 -0.0941 -2.7254 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9143 0.3450 -2.4664 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4228 -1.2649 -1.9270 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0383 2.5064 -0.8703 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4638 2.1201 -1.8388 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3796 2.5332 1.1804 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1647 3.4442 -0.1199 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7759 2.0817 1.0395 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8992 2.7250 -1.1757 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9437 -0.2115 -1.3190 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2925 -1.7424 -0.5032 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6952 -0.8741 0.1376 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1270 0.6004 2.2355 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6339 -1.1532 2.0317 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4646 0.0388 2.6638 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0210 0.5349 1.3527 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6273 -1.8948 1.5855 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9992 -2.1423 -0.1136 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7219 -0.6152 2.1397 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2398 -2.3505 1.7523 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1475 -3.0591 -0.3120 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3798 -2.4682 -0.9630 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1457 -1.9715 -1.7009 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0238 0.8161 0.7912 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4818 1.5482 -1.5677 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 2 4 1 0 4 5 1 0 6 5 1 1 6 7 1 0 7 8 1 0 8 9 1 0 9 10 1 1 9 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 6 15 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 19 21 1 0 21 22 1 0 21 23 1 0 21 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 6 11 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 32 33 2 0 30 2 1 0 29 6 1 0 32 6 1 0 27 9 1 0 27 14 1 0 24 15 1 0 1 34 1 0 1 35 1 0 1 36 1 0 3 37 1 0 3 38 1 0 3 39 1 0 4 40 1 0 4 41 1 0 5 42 1 0 5 43 1 0 7 44 1 0 7 45 1 0 8 46 1 0 8 47 1 0 10 48 1 0 10 49 1 0 10 50 1 0 11 51 1 6 12 52 1 0 12 53 1 0 13 54 1 0 13 55 1 0 14 56 1 1 16 57 1 0 16 58 1 0 16 59 1 0 17 60 1 0 17 61 1 0 18 62 1 0 18 63 1 0 19 64 1 1 20 65 1 0 22 66 1 0 22 67 1 0 22 68 1 0 23 69 1 0 23 70 1 0 23 71 1 0 24 72 1 1 25 73 1 0 25 74 1 0 26 75 1 0 26 76 1 0 28 77 1 0 28 78 1 0 28 79 1 0 29 80 1 1 30 81 1 6 M END

Standard InCHIKey	BVJDDPRBYGBPKD-TVZSAIOCSA-N
Standard InCHI	InChI=1S/C30H48O3/c1-25(2)14-16-30-17-15-28(6)18(22(30)23(25)33-24(30)32)8-9-20-27(5)12-11-21(31)26(3,4)19(27)10-13-29(20,28)7/h18-23,31H,8-17H2,1-7H3/t18-,19+,20-,21+,22+,23-,27+,28-,29-,30+/m1/s1
SMILES	CC1(C)CC[C@]23CC[C@]4(C)[C@H](CC[C@@H]5[C@@]6(C)CC[C@H](O)C(C)(C)[C@@H]6CC[C@]54C)[C@H]2[C@H]1OC3=O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	456.36	Volume:	499.831 ? Van der Waals volume.
Dense:	0.913	LogP:	4.779 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.412 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.679 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	0.0	Rigid Bonds:	30.0
TPSA:	46.53 ? Topological Polar Surface Area.	H-Bond Acceptor:	3.0
H-Bond Donor:	1.0	Rings:	6.0
Heavy Atoms:	3.0

MedChem Properties

QED Drug-Likeness Score:	0.409	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.58	Fsp³:	0.967
MCE-18:	118.068 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted	GSK Rule:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.961	Fluc inhibitor:	0.003 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.001 ? 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:	0.386	Promiscuous compounds:	0.063

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.241	MDCK Permeability:	-4.994
Pgp-inhibitor:	0.202	Pgp-substrate:	0.042
PAMPA:	0.917 ? 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):	0.001
20% Bioavailability (F20%):	0.259	30% Bioavailability (F30%):	0.119
50% Bioavailability (F50%):	0.978

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.605	MRP1:	0.95
Plasma Protein Binding (PPB):	97.8%	Volume Distribution (VD):	-0.008
Fu:	2.996% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.997	BCRP inhibitor:	0.023
BSEP inhibitor:	0.957

ADMET: Metabolism

CYP1A2-inhibitor:	0.556	CYP1A2-substrate:	0.032
CYP2C19-inhibitor:	0.969	CYP2C19-substrate:	0.404
CYP2C9-inhibitor:	0.053	CYP2C9-substrate:	0.025
CYP2D6-inhibitor:	0.167	CYP2D6-substrate:	0.036
CYP3A4-inhibitor:	0.181	CYP3A4-substrate:	0.996
CYP2B6-substrate:	0.002	CYP2C8-inhibitor:	0.836
HLM stability:	0.823 ? 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):

10.354

Half-life (T1/2):

0.443

ADMET: Toxicity

hERG Blockers:	0.067	hERG Blockers (10um):	0.276
Human Hepatotoxicity (H-HT):	0.557	Drug-induced Liver Injury (DILI):	0.273
AMES Toxicity:	0.4	Rat Oral Acute Toxicity:	0.388
Maximum Recommended Daily Dose:	0.572	Skin Sensitization:	0.978
Carcinogencity:	0.888	Eye Corrosion:	0.282
Eye Irritation:	0.597	Respiratory Toxicity:	0.789
Drug-induced Neurotoxicity:	0.083	Ototoxicity:	0.445
Hematotoxicity:	0.443	Drug-induced Nephrotoxicity:	0.854
Genotoxicity:	0.543	RPMI-8226 Immunitoxicity:	0.042
A549 Cytotoxicity:	0.333	Hek293 Cytotoxicity:	0.362
BCF:	2.572 ? 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:	4.718 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.847 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.64 ? 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
NPO8160	Diospyros montana	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17400463]
NPO8160	Diospyros montana	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10898	Diospyros morrisiana	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24185	Diospyros lotus	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24185	Diospyros lotus	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24185	Diospyros lotus	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24185	Diospyros lotus	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8160	Diospyros montana	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24185	Diospyros lotus	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10898	Diospyros morrisiana	Species	Ebenaceae	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
IC50	6

Activity Type	# Activity
Cell line	6

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
NPT306	Cell line	PC-3	Homo sapiens	IC50	>	50000.0	nM	PMID[19285391]
NPT579	Cell line	DLD-1	Homo sapiens	IC50	>	50000.0	nM	PMID[19285391]
NPT81	Cell line	A549	Homo sapiens	IC50	>	75000.0	nM	PMID[17614290]
NPT83	Cell line	MCF7	Homo sapiens	IC50	>	50000.0	nM	PMID[19285391]
NPT579	Cell line	DLD-1	Homo sapiens	IC50	>	75000.0	nM	PMID[17614290]
NPT81	Cell line	A549	Homo sapiens	IC50	>	50000.0	nM	PMID[19285391]

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 NPC603388 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	21297
0.1-0.2	24240
0.2-0.3	3766
0.3-0.4	455
0.4-0.5	71
0.5-0.6	23
0.6-0.7	1
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	Natural Product ID
0.7167	Intermediate Similarity	NPC62572
0.6724	Remote Similarity	NPC602784
0.5873	Remote Similarity	NPC12774
0.5714	Remote Similarity	NPC232112
0.5606	Remote Similarity	NPC483720
0.5606	Remote Similarity	NPC481321
0.5484	Remote Similarity	NPC58631
0.541	Remote Similarity	NPC97534
0.541	Remote Similarity	NPC195155
0.5224	Remote Similarity	NPC201406
0.5167	Remote Similarity	NPC142712
0.5156	Remote Similarity	NPC5767
0.5156	Remote Similarity	NPC475742
0.5156	Remote Similarity	NPC201725
0.5147	Remote Similarity	NPC131665
0.5147	Remote Similarity	NPC255387
0.5147	Remote Similarity	NPC112009
0.5082	Remote Similarity	NPC480925
0.5082	Remote Similarity	NPC48079
0.5077	Remote Similarity	NPC91387
0.5077	Remote Similarity	NPC74595
0.5077	Remote Similarity	NPC231680
0.5077	Remote Similarity	NPC270306
0.5077	Remote Similarity	NPC264665
0.5077	Remote Similarity	NPC269396

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC603388 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6966
0.1-0.2	2118
0.2-0.3	63
0.3-0.4	2
0.4-0.5	1
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