NPASS Compound

Natural Product: NPC102002

Natural Product ID	NPC102002
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	NFAUACMRIYFJJD-KZHHKZRASA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	102003238
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 96100 0 0 0 0 0 0 0 0999 V2000 5.5902 3.8757 1.0019 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1626 2.5003 0.6028 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8390 1.7751 -0.2705 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0634 2.3707 -0.8622 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4583 0.4480 -0.6805 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1029 -0.2147 -1.4977 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3413 -0.2253 -0.2098 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9152 -1.4870 -0.5529 C 0 0 1 0 0 0 0 0 0 0 0 0 4.0571 -2.5458 0.5073 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1485 -2.4543 1.6703 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5396 -3.7819 2.0754 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8145 -1.9074 2.9233 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9994 -1.5215 1.3275 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5714 -1.8238 -0.0663 C 0 0 1 0 0 0 0 0 0 0 0 0 0.2165 -1.3549 -0.4426 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7551 -2.2249 -0.4354 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1638 -1.9137 -0.7863 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3570 -0.5089 -0.2543 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.7999 -0.1339 -0.0929 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.6327 -0.2549 -1.2959 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3742 -1.1058 0.9433 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7282 -0.6949 1.4527 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8815 0.6977 1.8798 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.0240 1.7090 1.1818 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8200 2.5425 0.1952 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6130 2.7329 2.2613 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7936 1.2086 0.5740 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.2082 2.1542 -0.4253 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7319 1.8068 -0.4971 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4695 0.4020 -1.0190 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8157 0.4869 -2.4976 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0236 0.0352 -0.8114 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6004 1.0542 0.1118 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8114 0.1990 -2.0781 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1975 -0.3248 -2.0064 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5379 -1.4589 -1.1524 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5400 -2.6890 -2.1191 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2812 -2.7594 -2.7462 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0949 0.7153 -1.7818 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.2180 1.1038 1.6633 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0830 4.4166 0.1683 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2498 3.8457 1.8914 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6734 4.4131 1.3107 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2679 2.0529 1.0284 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8087 3.0185 -1.7363 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7697 1.5766 -1.1402 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5674 3.0420 -0.1217 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6271 -1.8269 -1.3447 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1433 -2.5711 0.7791 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8759 -3.5214 0.0139 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4122 -4.4796 1.2479 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1813 -4.2882 2.8353 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5541 -3.6014 2.5735 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9272 -2.0113 2.8489 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6235 -0.8108 2.9810 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4316 -2.3511 3.8429 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1496 -1.8263 1.9888 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3006 -0.5482 1.6176 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5396 -2.9615 -0.0182 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5561 -3.2921 -0.1526 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3791 -2.0136 -1.8651 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8269 -2.6584 -0.3004 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9603 -0.5356 0.7901 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9821 0.6800 -1.7630 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5594 -0.8216 -1.0751 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0901 -0.9146 -2.0307 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6054 -2.0455 0.3557 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6576 -1.3844 1.7134 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5374 -0.9571 0.7075 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9416 -1.3831 2.3078 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7665 0.7520 2.9957 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2039 3.2601 -0.3544 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5090 3.1745 0.8343 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5038 1.9491 -0.4311 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6448 3.2054 2.0269 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4114 2.1029 3.1767 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4179 3.4435 2.4717 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0250 1.1187 1.4050 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2189 3.1776 0.0420 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7176 2.2499 -1.3692 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4025 1.8632 0.5552 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3270 2.5883 -1.1641 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1251 1.1687 -3.0381 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7974 0.9970 -2.6482 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7640 -0.4831 -3.0213 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2931 1.0298 1.1357 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7260 1.0289 -0.0187 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3836 2.0370 -0.3430 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2249 -0.2891 -2.8944 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8519 1.2688 -2.3551 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4368 -0.5490 -3.1062 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6605 -3.6233 -1.5856 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2857 -2.5714 -2.9044 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9123 -3.6656 -2.7434 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0107 1.4056 -2.4857 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5144 0.6862 0.8092 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 3 4 1 0 3 5 1 0 5 6 2 0 5 7 1 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 10 12 1 0 10 13 1 0 13 14 1 0 14 15 1 0 15 16 2 0 16 17 1 0 17 18 1 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 24 26 1 0 24 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 1 6 30 32 1 0 32 33 1 1 32 34 1 0 34 35 1 0 35 36 1 0 36 37 1 6 37 38 1 0 35 39 1 0 23 40 1 0 36 8 1 0 36 14 1 0 32 15 1 0 30 18 1 0 27 19 1 0 1 41 1 0 1 42 1 0 1 43 1 0 2 44 1 0 4 45 1 0 4 46 1 0 4 47 1 0 8 48 1 6 9 49 1 0 9 50 1 0 11 51 1 0 11 52 1 0 11 53 1 0 12 54 1 0 12 55 1 0 12 56 1 0 13 57 1 0 13 58 1 0 14 59 1 1 16 60 1 0 17 61 1 0 17 62 1 0 18 63 1 1 20 64 1 0 20 65 1 0 20 66 1 0 21 67 1 0 21 68 1 0 22 69 1 0 22 70 1 0 23 71 1 1 25 72 1 0 25 73 1 0 25 74 1 0 26 75 1 0 26 76 1 0 26 77 1 0 27 78 1 1 28 79 1 0 28 80 1 0 29 81 1 0 29 82 1 0 31 83 1 0 31 84 1 0 31 85 1 0 33 86 1 0 33 87 1 0 33 88 1 0 34 89 1 0 34 90 1 0 35 91 1 6 37 92 1 0 37 93 1 0 38 94 1 0 39 95 1 0 40 96 1 0 M END

Standard InCHIKey	NFAUACMRIYFJJD-KZHHKZRASA-N
Standard InCHI	InChI=1S/C35H56O5/c1-10-21(2)29(39)40-28-19-30(3,4)17-23-22-11-12-25-32(7)15-14-26(37)31(5,6)24(32)13-16-33(25,8)34(22,9)18-27(38)35(23,28)20-36/h10-11,23-28,36-38H,12-20H2,1-9H3/b21-10+/t23-,24-,25+,26-,27+,28-,32-,33+,34+,35-/m0/s1
SMILES	C/C=C(C)/C(=O)O[C@H]1CC(C)(C)C[C@H]2C3=CC[C@@H]4[C@@]5(C)CC[C@@H](C(C)(C)[C@@H]5CC[C@@]4(C)[C@]3(C)C[C@H]([C@@]12CO)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	556.41	Volume:	607.175 ? Van der Waals volume.
Dense:	0.916	LogP:	4.812 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.251 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.655 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	4.0	Rigid Bonds:	28.0
TPSA:	86.99 ? Topological Polar Surface Area.	H-Bond Acceptor:	5.0
H-Bond Donor:	3.0	Rings:	5.0
Heavy Atoms:	5.0

MedChem Properties

QED Drug-Likeness Score:	0.207	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.192	Fsp³:	0.857
MCE-18:	109.846 ? 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:	0.719	Fluc inhibitor:	0.003 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.004 ? 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:	0.35	Promiscuous compounds:	0.259

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.415	MDCK Permeability:	-5.062
Pgp-inhibitor:	0.303	Pgp-substrate:	0.851
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):	0.121
20% Bioavailability (F20%):	0.998	30% Bioavailability (F30%):	0.965
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.166	MRP1:	0.796
Plasma Protein Binding (PPB):	94.925%	Volume Distribution (VD):	-0.083
Fu:	5.108% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.458	BCRP inhibitor:	0.573
BSEP inhibitor:	0.947

ADMET: Metabolism

CYP1A2-inhibitor:	0.13	CYP1A2-substrate:	0.01
CYP2C19-inhibitor:	0.786	CYP2C19-substrate:	0.969
CYP2C9-inhibitor:	0.003	CYP2C9-substrate:	0.001
CYP2D6-inhibitor:	0.013	CYP2D6-substrate:	0.109
CYP3A4-inhibitor:	0.011	CYP3A4-substrate:	0.177
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.715
HLM stability:	0.953 ? 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):

8.611

Half-life (T1/2):

0.913

ADMET: Toxicity

hERG Blockers:	0.034	hERG Blockers (10um):	0.202
Human Hepatotoxicity (H-HT):	0.392	Drug-induced Liver Injury (DILI):	0.184
AMES Toxicity:	0.463	Rat Oral Acute Toxicity:	0.555
Maximum Recommended Daily Dose:	0.862	Skin Sensitization:	0.852
Carcinogencity:	0.837	Eye Corrosion:	0.008
Eye Irritation:	0.36	Respiratory Toxicity:	0.913
Drug-induced Neurotoxicity:	0.038	Ototoxicity:	0.603
Hematotoxicity:	0.397	Drug-induced Nephrotoxicity:	0.781
Genotoxicity:	0.744	RPMI-8226 Immunitoxicity:	0.084
A549 Cytotoxicity:	0.214	Hek293 Cytotoxicity:	0.36
BCF:	1.813 ? 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:	4.303 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.816 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.262 ? 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
NPO20274	Cynanchum formosanum	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20056	Pinus monophylla	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20274	Cynanchum formosanum	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20056	Pinus monophylla	Species	Pinaceae	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

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

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 NPC102002 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	17638
0.1-0.2	25834
0.2-0.3	5142
0.3-0.4	1013
0.4-0.5	182
0.5-0.6	28
0.6-0.7	12
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
0.7826	Intermediate Similarity	NPC294360
0.7746	Intermediate Similarity	NPC273668
0.7639	Intermediate Similarity	NPC473160
0.7534	Intermediate Similarity	NPC480921
0.726	Intermediate Similarity	NPC283343
0.6842	Remote Similarity	NPC480920
0.6494	Remote Similarity	NPC258547
0.6486	Remote Similarity	NPC480919
0.6471	Remote Similarity	NPC311078
0.6377	Remote Similarity	NPC253807
0.6377	Remote Similarity	NPC158662
0.6364	Remote Similarity	NPC88349
0.6351	Remote Similarity	NPC164349
0.6234	Remote Similarity	NPC475263
0.6111	Remote Similarity	NPC473159
0.6081	Remote Similarity	NPC488519
0.6	Remote Similarity	NPC34177
0.5976	Remote Similarity	NPC474190
0.5854	Remote Similarity	NPC603645
0.5833	Remote Similarity	NPC159168
0.5775	Remote Similarity	NPC101475
0.5714	Remote Similarity	NPC49776
0.5714	Remote Similarity	NPC63118
0.5714	Remote Similarity	NPC474436
0.5694	Remote Similarity	NPC235341
0.5676	Remote Similarity	NPC246708
0.5571	Remote Similarity	NPC290598
0.5571	Remote Similarity	NPC30590
0.5432	Remote Similarity	NPC175006
0.5405	Remote Similarity	NPC470588
0.5366	Remote Similarity	NPC471433
0.5366	Remote Similarity	NPC86368
0.5366	Remote Similarity	NPC471432
0.5244	Remote Similarity	NPC488518
0.5238	Remote Similarity	NPC476132
0.5225	Remote Similarity	NPC265841
0.52	Remote Similarity	NPC238992
0.5135	Remote Similarity	NPC196753
0.5133	Remote Similarity	NPC484059
0.5133	Remote Similarity	NPC484060
0.5133	Remote Similarity	NPC476779
0.5122	Remote Similarity	NPC488520
0.5067	Remote Similarity	NPC480924
0.506	Remote Similarity	NPC480923
0.5057	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 NPC102002 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6851
0.1-0.2	2237
0.2-0.3	58
0.3-0.4	3
0.4-0.5	0
0.5-0.6	1
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
0.5658	Remote Similarity	NPD7645	Phase 2

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