NPASS Compound

Natural Product: NPC474989

Natural Product ID	NPC474989
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Olean-12-En-3Beta,15Alpha-Diol
IUPAC Name	(3S,4aR,6aR,6bS,7S,8aR,12aR,14aR,14bR)-4,4,6a,6b,8a,11,11,14b-octamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicene-3,7-diol
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL491188
PubChem CID	15601738
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 82 86 0 0 0 0 0 0 0 0999 V2000 6.5617 -1.3729 -0.6149 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2594 -1.1616 -1.1296 C 0 0 1 0 0 0 0 0 0 0 0 0 4.4307 -2.3108 -0.7015 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9632 -2.0534 -0.5972 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6668 -0.7802 0.2288 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3515 0.3017 -0.5580 C 0 0 2 0 0 0 0 0 0 0 0 0 4.8324 0.1876 -0.6661 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5806 0.6750 0.5436 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2178 1.1558 -1.8077 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8938 1.6893 -0.1792 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4355 1.7481 -0.6626 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6613 0.8100 0.2084 C 0 0 2 0 0 0 0 0 0 0 0 0 1.2129 -0.5751 0.3125 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6113 -1.1937 1.5741 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8615 -1.1014 1.4436 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5039 -0.2767 0.6233 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7756 0.6696 -0.2767 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8003 0.0032 -1.6556 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4477 1.9846 -0.4153 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0960 2.4927 -1.6898 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9467 1.9323 -0.3824 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5107 1.0641 0.7041 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.9793 -0.3243 0.6125 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5369 -1.0363 -0.5974 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0434 -1.1631 -0.3542 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2596 -1.9266 0.9137 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6403 -1.9325 -1.5045 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6576 0.2174 -0.3275 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0170 1.1290 0.6553 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1162 1.6247 2.0615 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5664 1.4998 1.5698 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2858 -1.0615 1.5574 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5904 -2.1068 0.0267 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4127 -1.2038 -2.2493 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5344 -3.1221 -1.4853 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8408 -2.8204 0.2212 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4992 -2.9303 -0.1020 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5079 -1.9779 -1.5971 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9771 0.1533 -1.6203 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9197 1.0119 1.3691 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3324 -0.0939 0.8926 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2306 1.5761 0.3312 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4132 2.1644 -1.3808 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1870 0.8224 -2.2643 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 1.2498 -2.5387 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4684 2.4025 -0.7993 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9575 1.8989 0.8967 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0311 2.7712 -0.4796 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4596 1.5264 -1.7222 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7347 -1.1738 -0.5231 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9790 -0.7499 2.4940 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8379 -2.3001 1.6009 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4498 -1.7795 2.0881 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4399 0.5694 -2.3724 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1234 -1.0580 -1.6087 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2084 -0.0223 -2.1205 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1330 2.7706 0.2931 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8677 2.5620 -2.2901 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3242 2.9693 -0.1950 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3669 1.6441 -1.3699 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3697 -0.8832 1.5029 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1530 -2.0681 -0.6745 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4416 -0.4498 -1.5305 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3596 -1.2532 1.8085 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1526 -2.5912 0.8310 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3843 -2.6094 1.1127 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7414 -1.9595 -1.3644 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3441 -1.4250 -2.4530 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2700 -2.9922 -1.4917 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6404 0.6018 -1.3600 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7229 0.0920 -0.0463 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3880 0.8892 1.6835 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2864 2.1831 0.3827 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6900 0.8155 2.7250 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9523 2.1392 2.5662 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3269 2.3773 1.8932 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2759 1.1700 2.1755 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5013 2.6025 1.4663 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4746 1.3364 2.1777 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3643 -1.3139 1.4997 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8141 -2.0094 1.9427 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1738 -0.3202 2.3337 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 7 9 1 0 6 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 2 0 16 17 1 0 17 18 1 6 17 19 1 0 19 20 1 0 19 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 25 27 1 0 25 28 1 0 28 29 1 0 22 30 1 1 12 31 1 1 5 32 1 1 7 2 1 0 17 12 1 0 29 22 1 0 13 5 1 0 23 16 1 0 1 33 1 0 2 34 1 6 3 35 1 0 3 36 1 0 4 37 1 0 4 38 1 0 6 39 1 6 8 40 1 0 8 41 1 0 8 42 1 0 9 43 1 0 9 44 1 0 9 45 1 0 10 46 1 0 10 47 1 0 11 48 1 0 11 49 1 0 13 50 1 6 14 51 1 0 14 52 1 0 15 53 1 0 18 54 1 0 18 55 1 0 18 56 1 0 19 57 1 1 20 58 1 0 21 59 1 0 21 60 1 0 23 61 1 1 24 62 1 0 24 63 1 0 26 64 1 0 26 65 1 0 26 66 1 0 27 67 1 0 27 68 1 0 27 69 1 0 28 70 1 0 28 71 1 0 29 72 1 0 29 73 1 0 30 74 1 0 30 75 1 0 30 76 1 0 31 77 1 0 31 78 1 0 31 79 1 0 32 80 1 0 32 81 1 0 32 82 1 0 M END

Standard InCHIKey	XVKHGUQJCRRKSC-WXIGGWTCSA-N
Standard InCHI	InChI=1S/C30H50O2/c1-25(2)15-16-27(5)18-24(32)30(8)19(20(27)17-25)9-10-22-28(6)13-12-23(31)26(3,4)21(28)11-14-29(22,30)7/h9,20-24,31-32H,10-18H2,1-8H3/t20-,21-,22+,23-,24-,27+,28-,29+,30-/m0/s1
SMILES	O[C@H]1CC[C@]2([C@H](C1(C)C)CC[C@@]1([C@@H]2CC=C2[C@@]1(C)[C@@H](O)C[C@@]1([C@H]2CC(C)(C)CC1)C)C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	442.38	Volume:	499.598 ? Van der Waals volume.
Dense:	0.885	LogP:	4.815 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.279 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-6.014 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	0.0	Rigid Bonds:	26.0
TPSA:	40.46 ? Topological Polar Surface Area.	H-Bond Acceptor:	2.0
H-Bond Donor:	2.0	Rings:	5.0
Heavy Atoms:	2.0

MedChem Properties

QED Drug-Likeness Score:	0.391	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.846	Fsp³:	0.933
MCE-18:	104.897 ? 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:	0.793	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.035 ? 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:	0.56	Promiscuous compounds:	0.086

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.281	MDCK Permeability:	-4.959
Pgp-inhibitor:	0.267	Pgp-substrate:	0.131
PAMPA:	0.985 ? 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%):	0.831	30% Bioavailability (F30%):	0.196
50% Bioavailability (F50%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.995	MRP1:	0.898
Plasma Protein Binding (PPB):	97.812%	Volume Distribution (VD):	-0.008
Fu:	2.239% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.989	BCRP inhibitor:	0.353
BSEP inhibitor:	0.938

ADMET: Metabolism

CYP1A2-inhibitor:	0.012	CYP1A2-substrate:	0.829
CYP2C19-inhibitor:	0.998	CYP2C19-substrate:	0.95
CYP2C9-inhibitor:	0.004	CYP2C9-substrate:	0.009
CYP2D6-inhibitor:	0.192	CYP2D6-substrate:	0.045
CYP3A4-inhibitor:	0.029	CYP3A4-substrate:	0.669
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.738
HLM stability:	0.977 ? 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):

11.192

Half-life (T1/2):

0.384

ADMET: Toxicity

hERG Blockers:	0.076	hERG Blockers (10um):	0.306
Human Hepatotoxicity (H-HT):	0.56	Drug-induced Liver Injury (DILI):	0.326
AMES Toxicity:	0.63	Rat Oral Acute Toxicity:	0.715
Maximum Recommended Daily Dose:	0.691	Skin Sensitization:	0.948
Carcinogencity:	0.938	Eye Corrosion:	0.035
Eye Irritation:	0.572	Respiratory Toxicity:	0.941
Drug-induced Neurotoxicity:	0.198	Ototoxicity:	0.434
Hematotoxicity:	0.657	Drug-induced Nephrotoxicity:	0.818
Genotoxicity:	0.8	RPMI-8226 Immunitoxicity:	0.101
A549 Cytotoxicity:	0.853	Hek293 Cytotoxicity:	0.704
BCF:	2.574 ? 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:	4.29 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.265 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.981 ? 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
NPO18290	Phyllanthus flexuosus	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11754608]
NPO18290	Phyllanthus flexuosus	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18290	Phyllanthus flexuosus	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18290	Phyllanthus flexuosus	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18290	Phyllanthus flexuosus	Species	Phyllanthaceae	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	1

Activity Type	# Activity
Individual protein	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1044	Individual protein	DNA topoisomerase II alpha	Homo sapiens	IC50	=	17500.0	nM	PMID[22608855]

In vitro activity

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

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 NPC474989 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	26511
0.1-0.2	19384
0.2-0.3	3145
0.3-0.4	622
0.4-0.5	139
0.5-0.6	32
0.6-0.7	12
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8333	Intermediate Similarity	NPC53744
0.7407	Intermediate Similarity	NPC290598
0.7407	Intermediate Similarity	NPC30590
0.7193	Intermediate Similarity	NPC480924
0.678	Remote Similarity	NPC238992
0.678	Remote Similarity	NPC470588
0.6724	Remote Similarity	NPC34177
0.661	Remote Similarity	NPC253807
0.661	Remote Similarity	NPC158662
0.6441	Remote Similarity	NPC101475
0.6333	Remote Similarity	NPC235341
0.629	Remote Similarity	NPC246708
0.6167	Remote Similarity	NPC311078
0.6167	Remote Similarity	NPC237344
0.6167	Remote Similarity	NPC196753
0.6	Remote Similarity	NPC488519
0.597	Remote Similarity	NPC480919
0.5714	Remote Similarity	NPC175006
0.5667	Remote Similarity	NPC27765
0.5667	Remote Similarity	NPC122418
0.5667	Remote Similarity	NPC491014
0.5625	Remote Similarity	NPC480950
0.5479	Remote Similarity	NPC480920
0.5469	Remote Similarity	NPC159168
0.5417	Remote Similarity	NPC273668
0.5362	Remote Similarity	NPC29765
0.5312	Remote Similarity	NPC475862
0.5211	Remote Similarity	NPC294360
0.5161	Remote Similarity	NPC120098
0.5161	Remote Similarity	NPC601696
0.5156	Remote Similarity	NPC132478
0.5147	Remote Similarity	NPC480946
0.5147	Remote Similarity	NPC130577
0.5147	Remote Similarity	NPC142415
0.5147	Remote Similarity	NPC102683
0.5147	Remote Similarity	NPC198664
0.5147	Remote Similarity	NPC2539
0.5143	Remote Similarity	NPC228784
0.5143	Remote Similarity	NPC324341
0.5143	Remote Similarity	NPC601810
0.5077	Remote Similarity	NPC478657
0.5072	Remote Similarity	NPC171203
0.5072	Remote Similarity	NPC307426
0.5072	Remote Similarity	NPC98442
0.5072	Remote Similarity	NPC242468
0.5068	Remote Similarity	NPC475263
0.5065	Remote Similarity	NPC474190
0.5065	Remote Similarity	NPC167383

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC474989 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	8129
0.1-0.2	977
0.2-0.3	39
0.3-0.4	4
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