NPASS Compound

Natural Product: NPC88116

Natural Product ID	NPC88116
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	2Alpha,3Beta,23-Trihydroxyolean-12-En-28-Oic Acid
IUPAC Name	(2R,4aS,6aR,6aS,6bR,8aR,9R,10R,11R,12aR,14bS)-10,11-dihydroxy-9-(hydroxymethyl)-2,6a,6b,9,12a-pentamethyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydro-1H-picene-4a-carboxylic acid
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL517732
PubChem CID	44566736
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 80 84 0 0 0 0 0 0 0 0999 V2000 -5.4450 2.5247 -1.9891 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1511 2.1052 -1.7256 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1513 0.7801 -0.9345 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.8911 -0.1785 -1.8849 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0158 0.9733 0.2457 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.2555 0.2899 0.1227 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4304 0.6327 1.5796 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.8206 1.5683 2.5761 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9484 0.5701 1.6457 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4269 -0.3209 0.5560 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.7647 0.3179 -0.7632 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.3183 -0.6967 -1.8106 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9021 -1.0833 -1.7514 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2186 -1.0617 -0.4301 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9046 -0.2719 0.6256 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3683 -0.5328 1.9969 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0970 -0.5222 1.9085 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8168 -0.4950 0.7679 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2007 -0.4721 -0.5639 C 0 0 2 0 0 0 0 0 0 0 0 0 1.1862 0.8914 -1.2063 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0347 -1.3238 -1.4945 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4049 -0.7023 -1.5326 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1147 -0.8317 -0.1958 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3112 -0.4817 0.9707 C 0 0 1 0 0 0 0 0 0 0 0 0 3.6057 0.7970 1.6892 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9392 1.3884 1.4386 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1601 1.3810 -0.0783 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4155 -0.0685 -0.3825 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0208 2.7830 1.9709 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5726 -2.2517 -0.1308 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3591 -3.0539 -1.0594 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2536 -2.6510 1.0164 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0170 -2.4761 0.1012 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9782 -1.6971 0.7089 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4599 3.1124 -2.7761 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5309 1.9921 -2.6391 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6579 2.9035 -1.1161 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9356 0.2535 -1.9346 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5096 -0.1110 -2.9117 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0055 -1.1802 -1.4828 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3562 2.0533 0.3394 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9514 0.8402 -0.2669 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9062 -0.3204 1.9594 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7500 1.3868 2.8616 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6758 0.2094 2.6598 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5433 1.5868 1.4731 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0912 1.1856 -0.9371 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0426 -1.5576 -1.8783 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4780 -0.1599 -2.7954 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8237 -2.1427 -2.1432 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2742 -0.4984 -2.4769 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6794 0.8099 0.4588 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6435 0.3443 2.6585 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7985 -1.4050 2.5091 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6261 -0.5385 2.8720 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5284 0.8652 -2.2855 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2265 1.3930 -1.2573 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8869 1.5998 -0.7211 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6333 -1.2264 -2.5454 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1440 -2.3642 -1.2283 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9913 -1.2846 -2.2925 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4428 0.3362 -1.8511 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4808 -1.2936 1.7490 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8375 1.6003 1.4746 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5158 0.6832 2.8140 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7474 0.7914 1.9239 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0215 2.0298 -0.3427 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2551 1.7904 -0.5516 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7727 -0.2161 -1.4157 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1869 -0.4383 0.3281 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7050 3.3649 1.3034 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0479 3.3143 1.9550 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4886 2.8002 2.9768 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3866 -3.6608 1.1230 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5934 -2.7262 0.9796 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2591 -3.2090 -0.6941 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0582 -2.6400 0.4495 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0867 -1.6489 0.6732 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7025 -2.4116 -0.0642 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7468 -2.0433 1.7418 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 3 2 1 6 3 4 1 0 3 5 1 0 5 6 1 0 5 7 1 0 7 8 1 0 7 9 1 0 9 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 1 0 16 17 1 0 17 18 2 0 18 19 1 0 19 20 1 6 19 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 26 29 1 0 23 30 1 1 30 31 2 0 30 32 1 0 14 33 1 1 10 34 1 6 11 3 1 0 19 14 1 0 28 23 1 0 15 10 1 0 24 18 1 0 1 35 1 0 2 36 1 0 2 37 1 0 4 38 1 0 4 39 1 0 4 40 1 0 5 41 1 1 6 42 1 0 7 43 1 1 8 44 1 0 9 45 1 0 9 46 1 0 11 47 1 6 12 48 1 0 12 49 1 0 13 50 1 0 13 51 1 0 15 52 1 6 16 53 1 0 16 54 1 0 17 55 1 0 20 56 1 0 20 57 1 0 20 58 1 0 21 59 1 0 21 60 1 0 22 61 1 0 22 62 1 0 24 63 1 1 25 64 1 0 25 65 1 0 26 66 1 1 27 67 1 0 27 68 1 0 28 69 1 0 28 70 1 0 29 71 1 0 29 72 1 0 29 73 1 0 32 74 1 0 33 75 1 0 33 76 1 0 33 77 1 0 34 78 1 0 34 79 1 0 34 80 1 0 M END

Standard InCHIKey	WDMZJJWHBHUUCS-DPBPPFMOSA-N
Standard InCHI	InChI=1S/C29H46O5/c1-17-8-11-29(24(33)34)13-12-27(4)18(19(29)14-17)6-7-22-25(2)15-20(31)23(32)26(3,16-30)21(25)9-10-28(22,27)5/h6,17,19-23,30-32H,7-16H2,1-5H3,(H,33,34)/t17-,19+,20-,21-,22-,23+,25+,26+,27-,28-,29+/m1/s1
SMILES	OC[C@]1(C)[C@@H](O)[C@H](O)C[C@]2([C@H]1CC[C@@]1([C@@H]2CC=C2[C@@]1(C)CC[C@@]1([C@H]2C[C@@H](CC1)C)C(=O)O)C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	474.33	Volume:	506.036 ? Van der Waals volume.
Dense:	0.937	LogP:	2.905 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.887 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.703 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	2.0	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:	0.432	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.994	Fsp³:	0.897
MCE-18:	103.636 ? 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:	0.724	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.017 ? 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:	0.361	Promiscuous compounds:	0.088

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.564	MDCK Permeability:	-5.083
Pgp-inhibitor:	0.002	Pgp-substrate:	0.016
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):	0.009
20% Bioavailability (F20%):	0.522	30% Bioavailability (F30%):	0.053
50% Bioavailability (F50%):	0.988

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.655	MRP1:	0.884
Plasma Protein Binding (PPB):	82.936%	Volume Distribution (VD):	-0.32
Fu:	15.825% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.075	BCRP inhibitor:	0.164
BSEP inhibitor:	0.953

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.002	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.001	CYP3A4-substrate:	0.061
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.005
HLM stability:	0.002 ? 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):

3.26

Half-life (T1/2):

1.418

ADMET: Toxicity

hERG Blockers:	0.017	hERG Blockers (10um):	0.026
Human Hepatotoxicity (H-HT):	0.638	Drug-induced Liver Injury (DILI):	0.638
AMES Toxicity:	0.358	Rat Oral Acute Toxicity:	0.22
Maximum Recommended Daily Dose:	0.181	Skin Sensitization:	0.961
Carcinogencity:	0.846	Eye Corrosion:	0.013
Eye Irritation:	0.556	Respiratory Toxicity:	0.668
Drug-induced Neurotoxicity:	0.029	Ototoxicity:	0.814
Hematotoxicity:	0.337	Drug-induced Nephrotoxicity:	0.954
Genotoxicity:	0.265	RPMI-8226 Immunitoxicity:	0.028
A549 Cytotoxicity:	0.108	Hek293 Cytotoxicity:	0.07
BCF:	0.73 ? 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:	3.465 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.037 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.228 ? 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
NPO28952	Sapium haematospermum	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15104489]
NPO28952	Sapium haematospermum	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28952	Sapium haematospermum	Species	Euphorbiaceae	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
MIC	1

Activity Type	# Activity
Organism	1

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
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	>	128.0	ug.mL-1	DOI[10.1016/0960-894X(96)00317-4]

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 NPC88116 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	22418
0.1-0.2	23959
0.2-0.3	2776
0.3-0.4	402
0.4-0.5	179
0.5-0.6	70
0.6-0.7	29
0.7-0.8	0
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8387	Intermediate Similarity	NPC231063
0.8387	Intermediate Similarity	NPC282395
0.8387	Intermediate Similarity	NPC609452
0.7692	Intermediate Similarity	NPC32407
0.7692	Intermediate Similarity	NPC263548
0.7692	Intermediate Similarity	NPC606320
0.7576	Intermediate Similarity	NPC247139
0.7538	Intermediate Similarity	NPC173744
0.7538	Intermediate Similarity	NPC204961
0.7538	Intermediate Similarity	NPC73004
0.7273	Intermediate Similarity	NPC472149
0.7273	Intermediate Similarity	NPC110308
0.7121	Intermediate Similarity	NPC84319
0.7121	Intermediate Similarity	NPC52021
0.7121	Intermediate Similarity	NPC599947
0.7101	Intermediate Similarity	NPC20235
0.7101	Intermediate Similarity	NPC299996
0.7059	Intermediate Similarity	NPC201657
0.6912	Remote Similarity	NPC145667
0.6765	Remote Similarity	NPC37221
0.6761	Remote Similarity	NPC479743
0.6618	Remote Similarity	NPC307282
0.6522	Remote Similarity	NPC71074
0.6522	Remote Similarity	NPC605937
0.6429	Remote Similarity	NPC259733
0.6429	Remote Similarity	NPC158371
0.6429	Remote Similarity	NPC207922
0.6377	Remote Similarity	NPC270768
0.6377	Remote Similarity	NPC59263
0.6377	Remote Similarity	NPC210106
0.6377	Remote Similarity	NPC121798
0.6377	Remote Similarity	NPC234346
0.6338	Remote Similarity	NPC88847
0.6286	Remote Similarity	NPC481314
0.6267	Remote Similarity	NPC188833
0.625	Remote Similarity	NPC130520
0.625	Remote Similarity	NPC481316
0.6197	Remote Similarity	NPC305464
0.6197	Remote Similarity	NPC19376
0.6197	Remote Similarity	NPC25848
0.6111	Remote Similarity	NPC9613
0.6056	Remote Similarity	NPC106112
0.6056	Remote Similarity	NPC261935
0.6056	Remote Similarity	NPC481360
0.6053	Remote Similarity	NPC96693
0.6027	Remote Similarity	NPC25299
0.6027	Remote Similarity	NPC481322
0.5972	Remote Similarity	NPC40092
0.5915	Remote Similarity	NPC182797
0.5915	Remote Similarity	NPC52169
0.5915	Remote Similarity	NPC488562
0.589	Remote Similarity	NPC191412
0.589	Remote Similarity	NPC114159
0.589	Remote Similarity	NPC6818
0.5867	Remote Similarity	NPC481315
0.5833	Remote Similarity	NPC61543
0.5833	Remote Similarity	NPC293048
0.5833	Remote Similarity	NPC225585
0.5775	Remote Similarity	NPC480946
0.5775	Remote Similarity	NPC130577
0.5775	Remote Similarity	NPC142415
0.5775	Remote Similarity	NPC102683
0.5735	Remote Similarity	NPC478657
0.5733	Remote Similarity	NPC116457
0.5733	Remote Similarity	NPC117663
0.5694	Remote Similarity	NPC282616
0.5694	Remote Similarity	NPC229281
0.5694	Remote Similarity	NPC306541
0.5694	Remote Similarity	NPC32118
0.5616	Remote Similarity	NPC158141
0.56	Remote Similarity	NPC607666
0.56	Remote Similarity	NPC608261
0.56	Remote Similarity	NPC611078
0.5556	Remote Similarity	NPC474806
0.5556	Remote Similarity	NPC133579
0.5541	Remote Similarity	NPC87095
0.5541	Remote Similarity	NPC136697
0.5541	Remote Similarity	NPC298554
0.5526	Remote Similarity	NPC481318
0.5479	Remote Similarity	NPC275809
0.5467	Remote Similarity	NPC35239
0.5429	Remote Similarity	NPC604575
0.5417	Remote Similarity	NPC43686
0.5405	Remote Similarity	NPC130278
0.5405	Remote Similarity	NPC111214
0.5395	Remote Similarity	NPC127689
0.5395	Remote Similarity	NPC62516
0.5333	Remote Similarity	NPC202728
0.5333	Remote Similarity	NPC158059
0.5333	Remote Similarity	NPC293564
0.5316	Remote Similarity	NPC481320
0.527	Remote Similarity	NPC51700
0.527	Remote Similarity	NPC37038
0.527	Remote Similarity	NPC88716
0.527	Remote Similarity	NPC68160
0.5263	Remote Similarity	NPC132824
0.525	Remote Similarity	NPC481319
0.52	Remote Similarity	NPC271614
0.5195	Remote Similarity	NPC148964
0.5135	Remote Similarity	NPC96916
0.5135	Remote Similarity	NPC187722
0.5132	Remote Similarity	NPC256247
0.5132	Remote Similarity	NPC173089
0.5128	Remote Similarity	NPC187933
0.5128	Remote Similarity	NPC324063
0.5128	Remote Similarity	NPC157113
0.5128	Remote Similarity	NPC174663
0.5128	Remote Similarity	NPC284865
0.5128	Remote Similarity	NPC600832
0.5125	Remote Similarity	NPC230151
0.5068	Remote Similarity	NPC280654
0.5067	Remote Similarity	NPC64872
0.5067	Remote Similarity	NPC25906
0.5067	Remote Similarity	NPC606443
0.5065	Remote Similarity	NPC263393
0.5063	Remote Similarity	NPC6255
0.5062	Remote Similarity	NPC233012

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC88116 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6288
0.1-0.2	2809
0.2-0.3	49
0.3-0.4	3
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