NPASS Compound

Natural Product: NPC16377

Natural Product ID	NPC16377
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	9-Hydroxy-1-(1-Hydroxymethyl-Vinyl)-5A,5B,8,8,11A-Pentamethyl-Icosahydro-Cyclopenta[A]Chrysene-3A-Carboxylic Acid
IUPAC Name	(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bS)-9-hydroxy-1-(3-hydroxyprop-1-en-2-yl)-5a,5b,8,8,11a-pentamethyl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a-carboxylic acid
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL77559
PubChem CID	11590966
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 -3.9313 2.0382 2.1483 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5266 1.6601 1.0726 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6430 2.5187 0.5220 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3129 2.9469 -0.7783 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2169 0.4494 0.2701 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.4061 -0.5300 0.4764 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8035 -1.8326 0.9264 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4395 -1.7567 0.2490 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4633 -2.7541 0.8172 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0927 -2.4646 0.3099 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7012 -1.0030 0.4373 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5018 -0.7945 1.9214 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7492 -0.0663 -0.0561 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.3327 1.3473 0.1043 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0480 1.6453 -0.4365 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0522 0.6249 0.0449 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4678 0.9400 -0.2816 C 0 0 1 0 0 0 0 0 0 0 0 0 2.7500 1.3452 -1.6775 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8648 2.1231 0.6205 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2946 2.4906 0.5241 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2637 1.4072 0.2420 C 0 0 1 0 0 0 0 0 0 0 0 0 4.7592 0.0231 0.3533 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2243 -0.5705 1.7014 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5348 -0.8164 -0.6773 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3097 -0.2039 0.2461 C 0 0 2 0 0 0 0 0 0 0 0 0 2.9452 -1.4468 -0.5441 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5615 -1.8455 -0.0761 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5628 -0.7439 -0.3448 C 0 0 1 0 0 0 0 0 0 0 0 0 0.2935 -0.8235 -1.8402 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9601 1.6375 -0.9735 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0576 -0.3588 0.6852 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.6657 -1.9249 -1.1777 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8484 -1.9875 -1.6877 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6870 -2.0453 -2.1723 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2143 2.9509 2.6555 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1448 1.4697 2.6065 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8284 3.3823 1.1596 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5548 1.8959 0.4166 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0883 3.4608 -1.0924 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1232 0.7197 -0.8005 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0766 -0.1034 1.2751 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0160 -0.5650 -0.4262 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7132 -1.8360 2.0125 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3972 -2.6882 0.5294 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7817 -3.7541 0.4008 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5977 -2.8208 1.8889 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9120 -2.8969 -0.6768 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3759 -3.0141 0.9937 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6446 0.2143 2.2874 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2786 -1.4110 2.4438 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4627 -1.2522 2.2917 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0581 -0.2544 -1.1276 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3667 1.6389 1.1656 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0591 1.9895 -0.4280 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3447 2.6157 -0.0063 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0002 1.7714 -1.5279 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9863 0.6610 1.1744 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4095 2.2646 -1.7266 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8695 1.6478 -2.2803 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2873 0.5983 -2.2976 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6046 1.7871 1.6527 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2650 3.0191 0.4250 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5352 3.0673 1.4684 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4007 3.2839 -0.2745 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1032 1.5321 0.9971 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5350 -1.3935 2.0015 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1850 0.2308 2.4692 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2580 -0.9237 1.6416 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0440 -0.8804 -1.6405 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6278 -1.8641 -0.2940 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5809 -0.4301 -0.7103 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8778 -0.3821 1.2805 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0057 -1.3074 -1.6272 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6289 -2.2617 -0.2233 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2481 -2.7250 -0.6762 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6443 -2.1373 0.9644 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0023 -1.8440 -2.1296 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2441 -0.6438 -2.4131 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4195 -0.1103 -2.2245 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6378 1.0852 -1.6976 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8745 -0.3526 1.7881 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7711 -2.6625 -2.9524 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 0 3 4 1 0 2 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 1 11 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 6 17 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 22 24 1 0 22 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 6 21 30 1 0 13 31 1 0 8 32 1 6 32 33 2 0 32 34 1 0 31 5 1 0 31 8 1 0 28 11 1 0 28 16 1 0 25 17 1 0 1 35 1 0 1 36 1 0 3 37 1 0 3 38 1 0 4 39 1 0 5 40 1 6 6 41 1 0 6 42 1 0 7 43 1 0 7 44 1 0 9 45 1 0 9 46 1 0 10 47 1 0 10 48 1 0 12 49 1 0 12 50 1 0 12 51 1 0 13 52 1 6 14 53 1 0 14 54 1 0 15 55 1 0 15 56 1 0 16 57 1 1 18 58 1 0 18 59 1 0 18 60 1 0 19 61 1 0 19 62 1 0 20 63 1 0 20 64 1 0 21 65 1 1 23 66 1 0 23 67 1 0 23 68 1 0 24 69 1 0 24 70 1 0 24 71 1 0 25 72 1 1 26 73 1 0 26 74 1 0 27 75 1 0 27 76 1 0 29 77 1 0 29 78 1 0 29 79 1 0 30 80 1 0 31 81 1 1 34 82 1 0 M END

Standard InCHIKey	NILZYBMKKVCAHD-FZFNOLFKSA-N
Standard InCHI	InChI=1S/C30H48O4/c1-18(17-31)19-9-14-30(25(33)34)16-15-28(5)20(24(19)30)7-8-22-27(4)12-11-23(32)26(2,3)21(27)10-13-29(22,28)6/h19-24,31-32H,1,7-17H2,2-6H3,(H,33,34)/t19-,20+,21-,22+,23-,24+,27-,28+,29+,30-/m0/s1
SMILES	C=C(CO)[C@@H]1CC[C@@]2(CC[C@]3(C)[C@H](CC[C@@H]4[C@@]5(C)CC[C@@H](C(C)(C)[C@@H]5CC[C@@]34C)O)[C@@H]12)C(=O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	472.36	Volume:	514.542 ? Van der Waals volume.
Dense:	0.918	LogP:	3.386 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.101 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.592 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	3.0	Rigid Bonds:	27.0
TPSA:	77.76 ? Topological Polar Surface Area.	H-Bond Acceptor:	4.0
H-Bond Donor:	3.0	Rings:	5.0
Heavy Atoms:	4.0

MedChem Properties

QED Drug-Likeness Score:	0.436	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.837	Fsp³:	0.9
MCE-18:	104.0 ? 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:	0.678	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.002 ? 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:	0.328	Promiscuous compounds:	0.111

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.421	MDCK Permeability:	-5.075
Pgp-inhibitor:	0.0	Pgp-substrate:	0.348
PAMPA:	0.998 ? 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):	0.004
20% Bioavailability (F20%):	0.583	30% Bioavailability (F30%):	0.564
50% Bioavailability (F50%):	0.99

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.558	MRP1:	0.915
Plasma Protein Binding (PPB):	94.743%	Volume Distribution (VD):	-0.398
Fu:	6.435% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.974
OATP1B3 inhibitor:	0.898	BCRP inhibitor:	0.266
BSEP inhibitor:	0.019

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.011	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.002	CYP3A4-substrate:	0.007
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.003
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):

5.344

Half-life (T1/2):

1.043

ADMET: Toxicity

hERG Blockers:	0.052	hERG Blockers (10um):	0.056
Human Hepatotoxicity (H-HT):	0.733	Drug-induced Liver Injury (DILI):	0.508
AMES Toxicity:	0.312	Rat Oral Acute Toxicity:	0.168
Maximum Recommended Daily Dose:	0.41	Skin Sensitization:	0.973
Carcinogencity:	0.946	Eye Corrosion:	0.066
Eye Irritation:	0.808	Respiratory Toxicity:	0.919
Drug-induced Neurotoxicity:	0.027	Ototoxicity:	0.653
Hematotoxicity:	0.446	Drug-induced Nephrotoxicity:	0.74
Genotoxicity:	0.482	RPMI-8226 Immunitoxicity:	0.019
A549 Cytotoxicity:	0.067	Hek293 Cytotoxicity:	0.128
BCF:	0.911 ? 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:	3.537 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.178 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.521 ? 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
NPO464	Oedera genistifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28085	Schima wallichi	Species	Theaceae	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
GI50	4
EC50	2

Activity Type	# Activity
Cell line	6

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
NPT393	Cell line	HCT-116	Homo sapiens	GI50	>	9800.0	nM	PMID[11527742]
NPT387	Cell line	M14	Homo sapiens	GI50	>	16200.0	nM	PMID[11527742]
NPT147	Cell line	SK-MEL-2	Homo sapiens	GI50	>	9300.0	nM	PMID[11527742]
NPT403	Cell line	UACC-257	Homo sapiens	GI50	>	50000.0	nM	PMID[11527742]
NPT306	Cell line	PC-3	Homo sapiens	EC50	>	8400000.0	nM	PMID[11527742]
NPT147	Cell line	SK-MEL-2	Homo sapiens	EC50	>	9000000.0	nM	PMID[11527742]

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 NPC16377 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	21502
0.1-0.2	23659
0.2-0.3	3799
0.3-0.4	637
0.4-0.5	176
0.5-0.6	53
0.6-0.7	13
0.7-0.8	0
0.8-0.85	0
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8772	High Similarity	NPC264317
0.8772	High Similarity	NPC294438
0.7742	Intermediate Similarity	NPC151191
0.7705	Intermediate Similarity	NPC488164
0.7705	Intermediate Similarity	NPC264005
0.7258	Intermediate Similarity	NPC30583
0.7231	Intermediate Similarity	NPC488165
0.7077	Intermediate Similarity	NPC601275
0.6923	Remote Similarity	NPC2783
0.6875	Remote Similarity	NPC476071
0.6667	Remote Similarity	NPC18064
0.6667	Remote Similarity	NPC472608
0.6615	Remote Similarity	NPC488506
0.6615	Remote Similarity	NPC220498
0.6515	Remote Similarity	NPC201655
0.6364	Remote Similarity	NPC213832
0.6212	Remote Similarity	NPC80590
0.6094	Remote Similarity	NPC68828
0.6087	Remote Similarity	NPC269360
0.6032	Remote Similarity	NPC248830
0.6032	Remote Similarity	NPC212241
0.5972	Remote Similarity	NPC603461
0.5882	Remote Similarity	NPC24772
0.5882	Remote Similarity	NPC211162
0.5882	Remote Similarity	NPC183374
0.5882	Remote Similarity	NPC291373
0.5882	Remote Similarity	NPC30322
0.5857	Remote Similarity	NPC475061
0.5857	Remote Similarity	NPC488213
0.5846	Remote Similarity	NPC119355
0.5821	Remote Similarity	NPC192744
0.5797	Remote Similarity	NPC271974
0.5797	Remote Similarity	NPC195395
0.5797	Remote Similarity	NPC247312
0.5775	Remote Similarity	NPC486704
0.5714	Remote Similarity	NPC4309
0.5694	Remote Similarity	NPC169933
0.5652	Remote Similarity	NPC474686
0.5606	Remote Similarity	NPC246445
0.5571	Remote Similarity	NPC277399
0.557	Remote Similarity	NPC486709
0.5556	Remote Similarity	NPC160506
0.5541	Remote Similarity	NPC481311
0.5479	Remote Similarity	NPC478841
0.5479	Remote Similarity	NPC488166
0.5479	Remote Similarity	NPC600004
0.5479	Remote Similarity	NPC608379
0.5429	Remote Similarity	NPC181225
0.5366	Remote Similarity	NPC486699
0.5352	Remote Similarity	NPC474512
0.5312	Remote Similarity	NPC192638
0.5312	Remote Similarity	NPC25511
0.5312	Remote Similarity	NPC600137
0.5303	Remote Similarity	NPC231256
0.5303	Remote Similarity	NPC178383
0.5294	Remote Similarity	NPC298168
0.5294	Remote Similarity	NPC143133
0.5278	Remote Similarity	NPC274330
0.5238	Remote Similarity	NPC290349
0.5224	Remote Similarity	NPC93662
0.5205	Remote Similarity	NPC474719
0.5147	Remote Similarity	NPC269396
0.5143	Remote Similarity	NPC119743
0.5135	Remote Similarity	NPC252714
0.5135	Remote Similarity	NPC611139
0.5125	Remote Similarity	NPC605397
0.5114	Remote Similarity	NPC51947
0.5114	Remote Similarity	NPC486700
0.5114	Remote Similarity	NPC275312
0.5077	Remote Similarity	NPC212733
0.5068	Remote Similarity	NPC57954
0.5068	Remote Similarity	NPC198664
0.5067	Remote Similarity	NPC293564
0.5067	Remote Similarity	NPC601176

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC16377 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5899
0.1-0.2	3147
0.2-0.3	93
0.3-0.4	7
0.4-0.5	1
0.5-0.6	2
0.6-0.7	0
0.7-0.8	0
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8772	High Similarity	NPD7520	Phase 1
0.5556	Remote Similarity	NPD8035	Phase 2
0.5233	Remote Similarity	NPD8034	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