NPASS Compound

Natural Product: NPC136697

Natural Product ID	NPC136697
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	MDDPTIWFHAUVPJ-ITSMGLEJSA-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] [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 84 88 0 0 0 0 0 0 0 0999 V2000 5.5958 1.3622 2.3435 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2405 0.5613 1.0755 C 0 0 2 0 0 0 0 0 0 0 0 0 5.3523 1.4833 -0.0720 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3881 1.3118 -1.1835 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7489 -0.0555 -1.1679 C 0 0 2 0 0 0 0 0 0 0 0 0 2.8247 -0.2441 -2.3325 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4489 0.2473 -2.2285 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8202 0.3600 -0.8866 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5716 1.8204 -0.4843 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6592 -0.1984 0.2090 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0967 -0.5165 1.3710 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3353 -0.3601 1.6791 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1423 -0.0399 0.4726 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6119 -0.4553 0.5948 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.8513 -1.9044 0.4848 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0538 -0.0607 2.0053 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4397 0.4287 2.1181 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3907 0.2209 1.0200 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.8488 0.2345 -0.3838 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4296 1.4167 -1.1710 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0833 2.6146 -0.5703 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.3747 -0.9811 -1.0737 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0055 -1.1776 -2.3732 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3734 0.4366 -0.3502 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6933 0.6661 -1.6503 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4473 -0.0774 -1.9420 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5198 -0.4049 -0.8278 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0758 -1.8501 -0.9387 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1933 -0.9417 1.2335 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1266 -0.4554 0.1172 C 0 0 2 0 0 0 0 0 0 0 0 0 3.8800 -0.0278 1.3328 C 0 0 1 0 0 0 0 0 0 0 0 0 4.1325 -1.1974 2.2992 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1699 0.9548 2.0670 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8820 -1.0132 -1.4258 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0549 -0.6386 -1.6246 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5996 -2.3651 -1.4409 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7285 1.9734 2.6146 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4844 1.9673 2.0691 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8865 0.6488 3.1481 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0379 -0.2445 1.0779 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3370 2.5543 0.2728 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3992 1.3688 -0.4830 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7060 2.1530 -1.2111 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9346 1.3499 -2.1777 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3237 0.2935 -3.1972 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8826 -1.3138 -2.6429 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8483 -0.4001 -2.9417 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3618 1.2713 -2.7044 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3430 2.2260 -0.9533 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6221 1.9576 0.6097 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3953 2.4308 -0.9064 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6877 -0.9269 2.1970 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6744 -1.2697 2.2173 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3778 0.4572 2.4600 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2139 1.0935 0.4662 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9506 -2.4315 0.9222 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6621 -2.2598 1.1934 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0045 -2.3233 -0.5002 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3860 0.7758 2.3608 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8019 -0.9023 2.7139 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4991 1.5011 2.4737 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8827 -0.1206 3.0145 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1912 1.0194 1.0992 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0880 1.4563 -2.2024 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5562 1.3709 -1.1172 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0341 2.4893 0.3992 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4980 -0.7870 -1.1337 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3555 -1.9047 -0.4436 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4825 -2.0343 -2.4128 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2995 1.4541 0.1771 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3842 0.4502 -2.5261 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4995 1.7686 -1.8605 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7486 -1.0500 -2.4403 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9541 0.4741 -2.7992 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2313 -2.3209 -0.0112 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8281 -1.9426 -1.6155 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8413 -2.4604 -1.5028 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8400 -1.4448 2.0187 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1751 -1.5939 0.1312 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2237 -1.4295 2.3945 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7085 -2.1540 1.8817 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7953 -0.9743 3.3204 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9373 1.7015 1.4934 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3110 -3.0716 -1.2396 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 20 21 1 0 19 22 1 0 22 23 1 0 19 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 1 18 29 1 0 10 30 1 0 30 31 1 0 31 32 1 0 31 33 1 1 5 34 1 6 34 35 2 0 34 36 1 0 31 2 1 0 30 5 1 0 27 8 1 0 27 13 1 0 24 14 1 0 1 37 1 0 1 38 1 0 1 39 1 0 2 40 1 6 3 41 1 0 3 42 1 0 4 43 1 0 4 44 1 0 6 45 1 0 6 46 1 0 7 47 1 0 7 48 1 0 9 49 1 0 9 50 1 0 9 51 1 0 11 52 1 0 12 53 1 0 12 54 1 0 13 55 1 6 15 56 1 0 15 57 1 0 15 58 1 0 16 59 1 0 16 60 1 0 17 61 1 0 17 62 1 0 18 63 1 6 20 64 1 0 20 65 1 0 21 66 1 0 22 67 1 0 22 68 1 0 23 69 1 0 24 70 1 1 25 71 1 0 25 72 1 0 26 73 1 0 26 74 1 0 28 75 1 0 28 76 1 0 28 77 1 0 29 78 1 0 30 79 1 6 32 80 1 0 32 81 1 0 32 82 1 0 33 83 1 0 36 84 1 0 M END

Standard InCHIKey	MDDPTIWFHAUVPJ-ITSMGLEJSA-N
Standard InCHI	InChI=1S/C30H48O6/c1-18-8-13-29(24(34)35)15-14-26(3)19(23(29)28(18,5)36)6-7-20-25(2)11-10-22(33)30(16-31,17-32)21(25)9-12-27(20,26)4/h6,18,20-23,31-33,36H,7-17H2,1-5H3,(H,34,35)/t18-,20-,21-,22+,23-,25-,26-,27-,28-,29+/m1/s1
SMILES	C[C@@H]1CC[C@@]2(CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)CC[C@@H](C(CO)(CO)[C@@H]5CC[C@@]34C)O)[C@@H]2[C@]1(C)O)C(=O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	504.35	Volume:	532.122 ? Van der Waals volume.
Dense:	0.948	LogP:	2.205 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.309 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.159 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	3.0	Rigid Bonds:	27.0
TPSA:	118.22 ? Topological Polar Surface Area.	H-Bond Acceptor:	6.0
H-Bond Donor:	5.0	Rings:	5.0
Heavy Atoms:	6.0

MedChem Properties

QED Drug-Likeness Score:	0.369	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.167	Fsp³:	0.9
MCE-18:	108.07 ? 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:	0.416	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.031 ? 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:	0.307	Promiscuous compounds:	0.215

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.609	MDCK Permeability:	-5.0
Pgp-inhibitor:	0.003	Pgp-substrate:	0.027
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):	0.117
20% Bioavailability (F20%):	0.949	30% Bioavailability (F30%):	0.193
50% Bioavailability (F50%):	0.992

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.125	MRP1:	0.986
Plasma Protein Binding (PPB):	69.696%	Volume Distribution (VD):	-0.286
Fu:	25.536% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.992
OATP1B3 inhibitor:	0.021	BCRP inhibitor:	0.003
BSEP inhibitor:	0.956

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.997	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.901	CYP3A4-substrate:	0.996
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.031
HLM stability:	0.0 ? 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):

2.877

Half-life (T1/2):

1.7

ADMET: Toxicity

hERG Blockers:	0.012	hERG Blockers (10um):	0.025
Human Hepatotoxicity (H-HT):	0.577	Drug-induced Liver Injury (DILI):	0.195
AMES Toxicity:	0.274	Rat Oral Acute Toxicity:	0.325
Maximum Recommended Daily Dose:	0.441	Skin Sensitization:	0.978
Carcinogencity:	0.952	Eye Corrosion:	0.004
Eye Irritation:	0.433	Respiratory Toxicity:	0.934
Drug-induced Neurotoxicity:	0.099	Ototoxicity:	0.738
Hematotoxicity:	0.516	Drug-induced Nephrotoxicity:	0.949
Genotoxicity:	0.724	RPMI-8226 Immunitoxicity:	0.037
A549 Cytotoxicity:	0.163	Hek293 Cytotoxicity:	0.162
BCF:	0.585 ? 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:	3.459 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.182 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.274 ? 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
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[16309325]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	n.a.	Seoul, Korea	2000-Jun	PMID[16643034]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	fruit	n.a.	n.a.	PMID[18505286]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	fruit	n.a.	n.a.	PMID[19650637]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	fruits	n.a.	n.a.	PMID[23305920]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32141747]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	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
EC50	1

Activity Type	# Activity
Cell line	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
NPT27675	Cell line	NRK-52E	Rattus norvegicus	EC50	=	1600.0	nM	PMID[32141747]

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 NPC136697 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	22997
0.1-0.2	22476
0.2-0.3	3480
0.3-0.4	557
0.4-0.5	234
0.5-0.6	61
0.6-0.7	33
0.7-0.8	0
0.8-0.85	1
0.85-0.9	5
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8871	High Similarity	NPC191412
0.8871	High Similarity	NPC114159
0.8871	High Similarity	NPC6818
0.871	High Similarity	NPC202728
0.871	High Similarity	NPC158059
0.8308	Intermediate Similarity	NPC187933
0.7612	Intermediate Similarity	NPC137072
0.7463	Intermediate Similarity	NPC118519
0.7463	Intermediate Similarity	NPC132824
0.7463	Intermediate Similarity	NPC247139
0.7353	Intermediate Similarity	NPC148964
0.7313	Intermediate Similarity	NPC259733
0.7313	Intermediate Similarity	NPC158371
0.7313	Intermediate Similarity	NPC207922
0.7101	Intermediate Similarity	NPC62516
0.7	Intermediate Similarity	NPC157113
0.6957	Remote Similarity	NPC35239
0.6912	Remote Similarity	NPC235053
0.6849	Remote Similarity	NPC96693
0.6849	Remote Similarity	NPC54909
0.6812	Remote Similarity	NPC256247
0.6761	Remote Similarity	NPC116457
0.6622	Remote Similarity	NPC233012
0.662	Remote Similarity	NPC118964
0.6575	Remote Similarity	NPC603658
0.6528	Remote Similarity	NPC284865
0.6429	Remote Similarity	NPC61543
0.6429	Remote Similarity	NPC293048
0.6429	Remote Similarity	NPC225585
0.6301	Remote Similarity	NPC147232
0.6286	Remote Similarity	NPC270768
0.6286	Remote Similarity	NPC59263
0.6286	Remote Similarity	NPC182797
0.6286	Remote Similarity	NPC210106
0.6286	Remote Similarity	NPC229281
0.6286	Remote Similarity	NPC51700
0.6286	Remote Similarity	NPC121798
0.6286	Remote Similarity	NPC88716
0.6286	Remote Similarity	NPC234346
0.6286	Remote Similarity	NPC68160
0.6286	Remote Similarity	NPC52169
0.6286	Remote Similarity	NPC488562
0.6154	Remote Similarity	NPC600756
0.6143	Remote Similarity	NPC480946
0.6143	Remote Similarity	NPC187722
0.6143	Remote Similarity	NPC130577
0.6143	Remote Similarity	NPC142415
0.6143	Remote Similarity	NPC102683
0.6111	Remote Similarity	NPC293564
0.5974	Remote Similarity	NPC327179
0.5946	Remote Similarity	NPC127689
0.5946	Remote Similarity	NPC130520
0.589	Remote Similarity	NPC298554
0.5811	Remote Similarity	NPC263393
0.5795	Remote Similarity	NPC482052
0.5753	Remote Similarity	NPC110308
0.5694	Remote Similarity	NPC274330
0.5658	Remote Similarity	NPC174663
0.5616	Remote Similarity	NPC171203
0.5616	Remote Similarity	NPC307426
0.5616	Remote Similarity	NPC98442
0.5616	Remote Similarity	NPC242468
0.5616	Remote Similarity	NPC606443
0.56	Remote Similarity	NPC9613
0.5541	Remote Similarity	NPC88116
0.5495	Remote Similarity	NPC482049
0.5495	Remote Similarity	NPC482050
0.5479	Remote Similarity	NPC198664
0.5467	Remote Similarity	NPC32407
0.5467	Remote Similarity	NPC263548
0.5467	Remote Similarity	NPC606320
0.5405	Remote Similarity	NPC275809
0.5385	Remote Similarity	NPC25491
0.5342	Remote Similarity	NPC477872
0.5333	Remote Similarity	NPC231063
0.5333	Remote Similarity	NPC282395
0.5333	Remote Similarity	NPC73489
0.5333	Remote Similarity	NPC130278
0.5333	Remote Similarity	NPC173744
0.5333	Remote Similarity	NPC204961
0.5333	Remote Similarity	NPC472149
0.5333	Remote Similarity	NPC73004
0.5333	Remote Similarity	NPC71074
0.5333	Remote Similarity	NPC37221
0.5333	Remote Similarity	NPC605937
0.5333	Remote Similarity	NPC609452
0.5269	Remote Similarity	NPC482051
0.5263	Remote Similarity	NPC173089
0.5263	Remote Similarity	NPC228784
0.5263	Remote Similarity	NPC324341
0.5263	Remote Similarity	NPC601810
0.52	Remote Similarity	NPC7260
0.52	Remote Similarity	NPC210037
0.52	Remote Similarity	NPC282616
0.52	Remote Similarity	NPC120968
0.52	Remote Similarity	NPC64872
0.52	Remote Similarity	NPC84319
0.52	Remote Similarity	NPC25906
0.52	Remote Similarity	NPC52021
0.52	Remote Similarity	NPC227467
0.52	Remote Similarity	NPC273621
0.52	Remote Similarity	NPC599947
0.5132	Remote Similarity	NPC38754
0.5132	Remote Similarity	NPC158141
0.5132	Remote Similarity	NPC481360
0.5065	Remote Similarity	NPC87095
0.5065	Remote Similarity	NPC477288
0.5063	Remote Similarity	NPC20235
0.5063	Remote Similarity	NPC299996
0.5063	Remote Similarity	NPC222047

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC136697 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6609
0.1-0.2	2485
0.2-0.3	51
0.3-0.4	2
0.4-0.5	3
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