NPASS Compound

Natural Product: NPC588837

Natural Product ID	NPC588837
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	18671-48-2
IUPAC Name	(2~{S},4~{a}~{R},6~{a}~{R},6~{a}~{S},6~{b}~{R},8~{a}~{R},10~{S},12~{a}~{R},14~{b}~{S})-10-hydroxy-2,6~{a},6~{b},9,9,12~{a}-hexamethyl-1,3,4,5,6,6~{a},7,8,8~{a},10,11,12,13,14~{b}-tetradecahydropicene-2,4~{a}-dicarboxylic acid
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
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 85 0 0 0 0 0 0 0 0999 V2000 -4.7526 1.0239 2.5241 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6651 0.4886 1.0822 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5808 1.3338 0.2685 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1869 -0.9227 1.1194 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.1783 -1.1728 0.1834 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0064 -1.8453 1.0118 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1819 -1.6839 -0.2215 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8001 -0.2140 -0.4894 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.5548 0.1687 -1.7391 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3244 -0.1879 -0.6002 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8328 -0.7697 -1.9227 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6003 -1.0425 -1.6833 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4072 -0.3590 -0.9121 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8135 -0.8265 -0.8306 C 0 0 2 0 0 0 0 0 0 0 0 0 3.1281 -1.7192 0.3210 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5350 -1.5913 0.8376 C 0 0 1 0 0 0 0 0 0 0 0 0 4.5336 -2.3547 2.1783 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4981 -2.3053 -0.0059 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0982 -2.9200 -1.0163 O 0 0 0 0 0 0 0 0 0 0 0 0 6.8444 -2.3180 0.2866 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8996 -0.1971 1.1658 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6124 0.7375 0.0746 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7007 0.3545 -1.0207 C 0 0 1 0 0 0 0 0 0 0 0 0 4.5731 0.1399 -2.2194 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8079 0.1375 -2.1069 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0304 -0.0613 -3.4843 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9076 1.5918 -1.4640 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7740 1.9661 -0.6017 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8697 0.8007 -0.1852 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0545 0.7403 1.3106 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5891 1.0976 -0.4365 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7059 2.0224 -1.6197 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1974 1.7988 0.7537 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7015 1.9505 0.6256 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2296 0.5358 0.7169 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.8604 0.6035 3.0518 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6319 0.5622 3.0486 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7839 2.1228 2.5381 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0370 0.8251 -0.6035 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4656 1.5917 0.9250 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1503 2.3309 0.0013 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6610 -1.1664 2.1169 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0174 -1.4948 0.5488 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4155 -2.8841 0.9877 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4291 -1.7795 1.9576 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7398 -2.1285 -1.0631 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2831 -2.3269 -0.0901 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9518 1.1889 -1.7334 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9563 -0.1062 -2.6278 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4719 -0.4866 -1.8503 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9457 -0.8735 0.1905 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9636 -0.0063 -2.7503 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4038 -1.6466 -2.2396 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9789 -1.9360 -2.2436 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0047 -1.5084 -1.7220 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0255 -2.8241 0.0870 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4155 -1.5763 1.1512 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2543 -3.4073 2.0380 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4473 -2.1799 2.7458 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6961 -1.8843 2.7633 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5105 -2.9316 -0.1667 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3623 0.0578 2.1257 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9992 -0.1903 1.3921 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6114 1.1335 -0.3016 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1929 1.6790 0.5659 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5009 -0.6232 -4.2006 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6060 1.5100 -2.5332 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6486 2.4208 -1.4403 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2196 2.7693 -1.1244 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1878 2.5125 0.2983 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7452 1.7409 1.6763 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1548 0.7372 1.5817 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5252 -0.0081 1.8576 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7575 3.0581 -1.2308 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7129 1.9058 -2.1308 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0045 1.8534 -2.4265 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8057 2.8048 0.9307 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1137 1.0996 1.6232 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0344 2.5135 -0.2295 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0320 2.4740 1.5462 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6678 0.0768 1.5885 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 4 6 1 0 6 7 1 0 7 8 1 0 8 9 1 6 8 10 1 0 10 11 1 0 11 12 1 0 12 13 2 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 1 16 18 1 0 18 19 2 0 18 20 1 0 16 21 1 0 21 22 1 0 22 23 1 0 23 24 1 6 24 25 2 0 24 26 1 0 23 27 1 0 27 28 1 0 28 29 1 0 29 30 1 1 29 31 1 0 31 32 1 6 31 33 1 0 33 34 1 0 34 35 1 0 35 2 1 0 35 8 1 0 31 10 1 0 29 13 1 0 23 14 1 0 1 36 1 0 1 37 1 0 1 38 1 0 3 39 1 0 3 40 1 0 3 41 1 0 4 42 1 1 5 43 1 0 6 44 1 0 6 45 1 0 7 46 1 0 7 47 1 0 9 48 1 0 9 49 1 0 9 50 1 0 10 51 1 1 11 52 1 0 11 53 1 0 12 54 1 0 14 55 1 6 15 56 1 0 15 57 1 0 17 58 1 0 17 59 1 0 17 60 1 0 20 61 1 0 21 62 1 0 21 63 1 0 22 64 1 0 22 65 1 0 26 66 1 0 27 67 1 0 27 68 1 0 28 69 1 0 28 70 1 0 30 71 1 0 30 72 1 0 30 73 1 0 32 74 1 0 32 75 1 0 32 76 1 0 33 77 1 0 33 78 1 0 34 79 1 0 34 80 1 0 35 81 1 1 M END

Standard InCHIKey	MCHKKYSPJGWAHQ-DQLFAPCQSA-N
Standard InCHI	InChI=1S/C30H46O5/c1-25(2)20-9-12-29(6)21(27(20,4)11-10-22(25)31)8-7-18-19-17-26(3,23(32)33)13-15-30(19,24(34)35)16-14-28(18,29)5/h7,19-22,31H,8-17H2,1-6H3,(H,32,33)(H,34,35)/t19-,20-,21+,22-,26-,27-,28+,29+,30-/m0/s1
SMILES	CC1(C)[C@@H](O)CC[C@]2(C)[C@H]3CC=C4[C@@H]5C[C@@](C)(C(=O)O)CC[C@]5(C(=O)O)CC[C@@]4(C)[C@]3(C)CC[C@@H]12

Calculated Properties

Physi-Chem Properties

Molecular Weight:	486.33	Volume:	520.695 ? Van der Waals volume.
Dense:	0.934	LogP:	2.889 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.625 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.267 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	2.0	Rigid Bonds:	28.0
TPSA:	94.83 ? 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:	0.398	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.725	Fsp³:	0.867
MCE-18:	108.571 ? 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:	0.899	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.029 ? 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:	0.392	Promiscuous compounds:	0.068

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.152	MDCK Permeability:	-4.864
Pgp-inhibitor:	0.0	Pgp-substrate:	0.109
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):	0.0
20% Bioavailability (F20%):	0.351	30% Bioavailability (F30%):	0.005
50% Bioavailability (F50%):	0.937

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.008	MRP1:	0.986
Plasma Protein Binding (PPB):	86.232%	Volume Distribution (VD):	-0.506
Fu:	11.757% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.994
OATP1B3 inhibitor:	0.001	BCRP inhibitor:	0.011
BSEP inhibitor:	0.323

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	0.061
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.794
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):

1.577

Half-life (T1/2):

1.789

ADMET: Toxicity

hERG Blockers:	0.011	hERG Blockers (10um):	0.01
Human Hepatotoxicity (H-HT):	0.697	Drug-induced Liver Injury (DILI):	0.412
AMES Toxicity:	0.046	Rat Oral Acute Toxicity:	0.142
Maximum Recommended Daily Dose:	0.526	Skin Sensitization:	0.975
Carcinogencity:	0.844	Eye Corrosion:	0.074
Eye Irritation:	0.783	Respiratory Toxicity:	0.909
Drug-induced Neurotoxicity:	0.002	Ototoxicity:	0.573
Hematotoxicity:	0.228	Drug-induced Nephrotoxicity:	0.889
Genotoxicity:	0.279	RPMI-8226 Immunitoxicity:	0.023
A549 Cytotoxicity:	0.011	Hek293 Cytotoxicity:	0.033
BCF:	0.733 ? 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:	3.634 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.162 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.326 ? 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
NPO47063	Phytolacca octandra	Species	Phytolaccaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]

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 NPC588837 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	22231
0.1-0.2	23096
0.2-0.3	3382
0.3-0.4	715
0.4-0.5	271
0.5-0.6	95
0.6-0.7	35
0.7-0.8	0
0.8-0.85	7
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8197	Intermediate Similarity	NPC480946
0.8197	Intermediate Similarity	NPC130577
0.8197	Intermediate Similarity	NPC142415
0.8197	Intermediate Similarity	NPC102683
0.8065	Intermediate Similarity	NPC182797
0.8065	Intermediate Similarity	NPC52169
0.8065	Intermediate Similarity	NPC488562
0.7344	Intermediate Similarity	NPC187722
0.7231	Intermediate Similarity	NPC51700
0.7231	Intermediate Similarity	NPC171203
0.7231	Intermediate Similarity	NPC88716
0.7231	Intermediate Similarity	NPC307426
0.7231	Intermediate Similarity	NPC98442
0.7231	Intermediate Similarity	NPC68160
0.7231	Intermediate Similarity	NPC242468
0.7231	Intermediate Similarity	NPC606443
0.7015	Intermediate Similarity	NPC202728
0.7015	Intermediate Similarity	NPC158059
0.7015	Intermediate Similarity	NPC293564
0.697	Remote Similarity	NPC270768
0.697	Remote Similarity	NPC59263
0.697	Remote Similarity	NPC210106
0.697	Remote Similarity	NPC121798
0.697	Remote Similarity	NPC234346
0.6923	Remote Similarity	NPC477872
0.6818	Remote Similarity	NPC198664
0.6765	Remote Similarity	NPC298554
0.6716	Remote Similarity	NPC7260
0.6716	Remote Similarity	NPC210037
0.6716	Remote Similarity	NPC120968
0.6716	Remote Similarity	NPC227467
0.6716	Remote Similarity	NPC273621
0.6571	Remote Similarity	NPC130520
0.6522	Remote Similarity	NPC228784
0.6522	Remote Similarity	NPC324341
0.6522	Remote Similarity	NPC601810
0.6471	Remote Similarity	NPC112866
0.6429	Remote Similarity	NPC263393
0.6324	Remote Similarity	NPC274330
0.6286	Remote Similarity	NPC136697
0.6232	Remote Similarity	NPC229281
0.6232	Remote Similarity	NPC64872
0.6232	Remote Similarity	NPC84319
0.6232	Remote Similarity	NPC25906
0.6232	Remote Similarity	NPC52021
0.6232	Remote Similarity	NPC599947
0.6184	Remote Similarity	NPC603645
0.6143	Remote Similarity	NPC61543
0.6143	Remote Similarity	NPC293048
0.6143	Remote Similarity	NPC225585
0.6143	Remote Similarity	NPC472149
0.6081	Remote Similarity	NPC474727
0.6	Remote Similarity	NPC282616
0.6	Remote Similarity	NPC275809
0.5972	Remote Similarity	NPC191412
0.5972	Remote Similarity	NPC114159
0.5972	Remote Similarity	NPC6818
0.5915	Remote Similarity	NPC158141
0.5915	Remote Similarity	NPC110308
0.589	Remote Similarity	NPC127689
0.5857	Remote Similarity	NPC610937
0.5833	Remote Similarity	NPC29765
0.5811	Remote Similarity	NPC187933
0.5811	Remote Similarity	NPC116457
0.5775	Remote Similarity	NPC195019
0.5753	Remote Similarity	NPC91010
0.5735	Remote Similarity	NPC604575
0.5698	Remote Similarity	NPC488215
0.5694	Remote Similarity	NPC231063
0.5694	Remote Similarity	NPC18872
0.5694	Remote Similarity	NPC282395
0.5694	Remote Similarity	NPC130278
0.5694	Remote Similarity	NPC290614
0.5694	Remote Similarity	NPC88116
0.5694	Remote Similarity	NPC609452
0.5616	Remote Similarity	NPC200752
0.5541	Remote Similarity	NPC118519
0.5479	Remote Similarity	NPC106112
0.5479	Remote Similarity	NPC261935
0.5479	Remote Similarity	NPC71074
0.5479	Remote Similarity	NPC37221
0.5479	Remote Similarity	NPC481360
0.5479	Remote Similarity	NPC605937
0.5455	Remote Similarity	NPC290598
0.5455	Remote Similarity	NPC27765
0.5455	Remote Similarity	NPC30590
0.5455	Remote Similarity	NPC122418
0.5455	Remote Similarity	NPC491014
0.5441	Remote Similarity	NPC101475
0.5405	Remote Similarity	NPC259733
0.5405	Remote Similarity	NPC158371
0.5405	Remote Similarity	NPC207922
0.5405	Remote Similarity	NPC155120
0.5405	Remote Similarity	NPC120840
0.5405	Remote Similarity	NPC288833
0.5395	Remote Similarity	NPC324063
0.5395	Remote Similarity	NPC222047
0.5366	Remote Similarity	NPC204407
0.5362	Remote Similarity	NPC235341
0.5349	Remote Similarity	NPC18982
0.5342	Remote Similarity	NPC37038
0.5333	Remote Similarity	NPC4036
0.5333	Remote Similarity	NPC65120
0.5333	Remote Similarity	NPC145067
0.5333	Remote Similarity	NPC233455
0.5333	Remote Similarity	NPC474963
0.5333	Remote Similarity	NPC158030
0.5333	Remote Similarity	NPC474525
0.5333	Remote Similarity	NPC610635
0.5316	Remote Similarity	NPC188833
0.5301	Remote Similarity	NPC283849
0.5301	Remote Similarity	NPC28198
0.5301	Remote Similarity	NPC476123
0.5301	Remote Similarity	NPC606107
0.5281	Remote Similarity	NPC198621
0.5281	Remote Similarity	NPC216940
0.5278	Remote Similarity	NPC242631
0.527	Remote Similarity	NPC38754
0.5263	Remote Similarity	NPC25299
0.5263	Remote Similarity	NPC481322
0.5224	Remote Similarity	NPC120098
0.5217	Remote Similarity	NPC311078
0.5205	Remote Similarity	NPC18064
0.52	Remote Similarity	NPC173089
0.5195	Remote Similarity	NPC157113
0.5176	Remote Similarity	NPC286347
0.5143	Remote Similarity	NPC253807
0.5143	Remote Similarity	NPC472608
0.5143	Remote Similarity	NPC40394
0.5143	Remote Similarity	NPC158662
0.5139	Remote Similarity	NPC280654
0.5139	Remote Similarity	NPC246708
0.5135	Remote Similarity	NPC156981
0.5132	Remote Similarity	NPC132824
0.5128	Remote Similarity	NPC96580
0.5125	Remote Similarity	NPC54909
0.5116	Remote Similarity	NPC100383
0.5114	Remote Similarity	NPC475627
0.507	Remote Similarity	NPC159168
0.507	Remote Similarity	NPC95594
0.5068	Remote Similarity	NPC477579
0.5067	Remote Similarity	NPC73489
0.5067	Remote Similarity	NPC173744
0.5067	Remote Similarity	NPC204961
0.5067	Remote Similarity	NPC73004
0.5065	Remote Similarity	NPC46441
0.5065	Remote Similarity	NPC137072
0.5065	Remote Similarity	NPC474529
0.5065	Remote Similarity	NPC148964

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC588837 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6402
0.1-0.2	2690
0.2-0.3	49
0.3-0.4	6
0.4-0.5	1
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
0.5333	Remote Similarity	NPD7515	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