NPASS Compound

Natural Product: NPC87604

Natural Product ID	NPC87604
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	24-Methylcholesta-5,24(28)-Diene-3Beta,19-Diol
IUPAC Name	(3S,8S,9S,10S,13R,14S,17R)-10-(hydroxymethyl)-13-methyl-17-[(2R)-6-methyl-5-methylideneheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL470130
PubChem CID	11212165
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0003567] Ergostane steroids [CHEMONTID:0001403] Ergosterols and derivatives

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 76 79 0 0 0 0 0 0 0 0999 V2000 -4.9955 2.5421 0.8641 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7779 1.8967 0.7394 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7969 0.7185 -0.1734 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.2396 1.2625 -1.5367 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5420 0.7267 -1.9954 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6367 0.7031 -0.9905 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.2202 0.1995 0.3805 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8141 -0.2534 0.2562 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5781 -1.5330 0.5237 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2453 -2.1436 0.4176 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1841 -1.1127 0.4569 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4230 0.1227 -0.3703 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.3316 1.0839 0.0032 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0416 0.5714 0.0752 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2519 -0.8082 0.5725 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8767 -1.6366 -0.0604 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5514 -3.0247 0.2634 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9750 -2.9946 0.4657 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3674 -1.5852 -0.0126 C 0 0 2 0 0 0 0 0 0 0 0 0 2.7610 -1.2436 0.1572 C 0 0 1 0 0 0 0 0 0 0 0 0 3.2371 0.0803 -0.3359 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7340 0.1535 -0.0284 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3356 1.4185 -0.4955 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5936 2.3131 -1.1107 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7653 1.7057 -0.2862 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5626 0.6308 -1.0097 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1514 1.7183 1.1831 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3283 -1.5323 1.5287 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0727 -0.9716 2.0586 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3915 1.8783 -0.9257 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0058 3.4715 0.5847 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0663 2.6914 0.4253 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4750 1.6245 1.7928 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3020 2.3727 -1.5449 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4866 1.0111 -2.3097 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8906 1.4113 -2.8262 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4505 -0.2726 -2.5135 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3808 -0.0634 -1.3759 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8569 -0.6941 0.6662 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4152 0.9107 1.1964 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3996 -2.1990 0.8445 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0768 -2.8178 1.2887 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2256 -2.7134 -0.5411 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1157 -0.7443 1.5179 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2816 -0.1590 -1.4336 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6168 1.4851 1.0217 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3747 1.9413 -0.6895 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5692 0.6799 -0.8891 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5895 1.2567 0.7918 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7870 -1.4743 -1.1536 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0742 -3.4739 1.1077 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7223 -3.6706 -0.6477 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1010 -3.1141 1.5549 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4872 -3.7411 -0.1458 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1140 -1.6512 -1.1308 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3491 -1.9778 -0.5016 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8226 0.9488 0.2038 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1341 0.1281 -1.4257 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2235 -0.7557 -0.3845 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8007 0.1645 1.0997 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5474 2.1184 -1.2717 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9919 3.2594 -1.4721 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0500 2.6967 -0.6870 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4274 -0.3330 -0.5161 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1559 0.6225 -2.0627 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6048 0.9874 -1.0679 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4022 2.2658 1.7823 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3034 0.6662 1.5472 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1040 2.2728 1.2618 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4360 -1.7716 1.4379 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3069 -0.6568 2.2061 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9198 -2.4493 1.9968 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5862 -1.8270 2.3305 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0121 -1.1663 2.6132 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4490 -0.0682 2.4665 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9864 1.9214 -1.7279 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 3 2 1 1 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 2 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 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 2 0 23 25 1 0 25 26 1 0 25 27 1 0 20 28 1 0 15 29 1 1 6 30 1 0 8 3 1 0 16 11 1 0 12 3 1 0 19 15 1 0 1 31 1 0 2 32 1 0 2 33 1 0 4 34 1 0 4 35 1 0 5 36 1 0 5 37 1 0 6 38 1 6 7 39 1 0 7 40 1 0 9 41 1 0 10 42 1 0 10 43 1 0 11 44 1 1 12 45 1 6 13 46 1 0 13 47 1 0 14 48 1 0 14 49 1 0 16 50 1 6 17 51 1 0 17 52 1 0 18 53 1 0 18 54 1 0 19 55 1 6 20 56 1 6 21 57 1 0 21 58 1 0 22 59 1 0 22 60 1 0 24 61 1 0 24 62 1 0 25 63 1 0 26 64 1 0 26 65 1 0 26 66 1 0 27 67 1 0 27 68 1 0 27 69 1 0 28 70 1 0 28 71 1 0 28 72 1 0 29 73 1 0 29 74 1 0 29 75 1 0 30 76 1 0 M END

Standard InCHIKey	WOOKNJANWWBKHW-TURLQYGPSA-N
Standard InCHI	InChI=1S/C28H46O2/c1-18(2)19(3)6-7-20(4)24-10-11-25-23-9-8-21-16-22(30)12-15-28(21,17-29)26(23)13-14-27(24,25)5/h8,18,20,22-26,29-30H,3,6-7,9-17H2,1-2,4-5H3/t20-,22+,23+,24-,25+,26+,27-,28-/m1/s1
SMILES	OC[C@]12CC[C@@H](CC1=CC[C@@H]1[C@@H]2CC[C@]2([C@H]1CC[C@@H]2[C@@H](CCC(=C)C(C)C)C)C)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	414.35	Volume:	470.926 ? Van der Waals volume.
Dense:	0.88	LogP:	5.749 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.52 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.182 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	21.0
TPSA:	40.46 ? Topological Polar Surface Area.	H-Bond Acceptor:	2.0
H-Bond Donor:	2.0	Rings:	4.0
Heavy Atoms:	2.0

MedChem Properties

QED Drug-Likeness Score:	0.485	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.586	Fsp³:	0.857
MCE-18:	69.577 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted	GSK Rule:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.756	Fluc inhibitor:	0.007 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.006 ? 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:	0.542	Promiscuous compounds:	0.027

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.024	MDCK Permeability:	-4.971
Pgp-inhibitor:	0.008	Pgp-substrate:	0.031
PAMPA:	0.002 ? 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%):	0.003	30% Bioavailability (F30%):	0.332
50% Bioavailability (F50%):	0.987

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.153	MRP1:	0.072
Plasma Protein Binding (PPB):	87.999%	Volume Distribution (VD):	-0.117
Fu:	12.232% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.842
BSEP inhibitor:	0.05

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.007
CYP2C19-inhibitor:	0.049	CYP2C19-substrate:	0.012
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.001
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.702
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.806 ? 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):

9.402

Half-life (T1/2):

1.285

ADMET: Toxicity

hERG Blockers:	0.093	hERG Blockers (10um):	0.249
Human Hepatotoxicity (H-HT):	0.528	Drug-induced Liver Injury (DILI):	0.19
AMES Toxicity:	0.18	Rat Oral Acute Toxicity:	0.097
Maximum Recommended Daily Dose:	0.612	Skin Sensitization:	0.957
Carcinogencity:	0.795	Eye Corrosion:	0.019
Eye Irritation:	0.829	Respiratory Toxicity:	0.757
Drug-induced Neurotoxicity:	0.064	Ototoxicity:	0.573
Hematotoxicity:	0.314	Drug-induced Nephrotoxicity:	0.364
Genotoxicity:	0.049	RPMI-8226 Immunitoxicity:	0.046
A549 Cytotoxicity:	0.171	Hek293 Cytotoxicity:	0.327
BCF:	2.39 ? 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:	4.339 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.371 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.028 ? 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
NPO25976	Dendronephthya gigantea	Species	Nephtheidae	Eukaryota	n.a.	n.a.	n.a.	PMID[10843584]
NPO25976	Dendronephthya gigantea	Species	Nephtheidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15497934]
NPO13916	Nephthea erecta	Species	Nephtheidae	Eukaryota	n.a.	formosan soft coral	n.a.	PMID[17845002]
NPO13916	Nephthea erecta	Species	Nephtheidae	Eukaryota	n.a.	Formosan soft coral	n.a.	PMID[24370010]
NPO25976	Dendronephthya gigantea	Species	Nephtheidae	Eukaryota	n.a.	n.a.	n.a.	PMID[30407007]
NPO13916	Nephthea erecta	Species	Nephtheidae	Eukaryota	n.a.	n.a.	n.a.	PMID[9722490]
NPO25976	Dendronephthya gigantea	Species	Nephtheidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13916	Nephthea erecta	Species	Nephtheidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25976	Dendronephthya gigantea	Species	Nephtheidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13916	Nephthea erecta	Species	Nephtheidae	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
ED50	4

Activity Type	# Activity
Cell line	4

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
NPT81	Cell line	A549	Homo sapiens	ED50	=	1.76	ug ml-1	PubChem BioAssay data set
NPT139	Cell line	HT-29	Homo sapiens	ED50	=	1.31	ug ml-1	PubChem BioAssay data set
NPT91	Cell line	KB	Homo sapiens	ED50	=	1.1	ug ml-1	PMID[15974609]
NPT168	Cell line	P388	Mus musculus	ED50	=	0.45	ug ml-1	PMID[15974609]

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 NPC87604 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	23675
0.1-0.2	22427
0.2-0.3	3406
0.3-0.4	229
0.4-0.5	73
0.5-0.6	30
0.6-0.7	15
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8148	Intermediate Similarity	NPC26117
0.7736	Intermediate Similarity	NPC134847
0.6842	Remote Similarity	NPC209620
0.678	Remote Similarity	NPC186688
0.6613	Remote Similarity	NPC234335
0.625	Remote Similarity	NPC162742
0.625	Remote Similarity	NPC304309
0.625	Remote Similarity	NPC470228
0.6207	Remote Similarity	NPC198968
0.614	Remote Similarity	NPC22105
0.614	Remote Similarity	NPC34019
0.614	Remote Similarity	NPC107059
0.6066	Remote Similarity	NPC477522
0.6034	Remote Similarity	NPC136188
0.6034	Remote Similarity	NPC28657
0.6034	Remote Similarity	NPC474216
0.6	Remote Similarity	NPC321381
0.5932	Remote Similarity	NPC230301
0.5932	Remote Similarity	NPC285893
0.5833	Remote Similarity	NPC241290
0.5833	Remote Similarity	NPC164840
0.5833	Remote Similarity	NPC484739
0.5833	Remote Similarity	NPC209944
0.5833	Remote Similarity	NPC155986
0.5738	Remote Similarity	NPC600056
0.5667	Remote Similarity	NPC84694
0.5667	Remote Similarity	NPC143182
0.5645	Remote Similarity	NPC472265
0.5645	Remote Similarity	NPC59453
0.5625	Remote Similarity	NPC278648
0.5574	Remote Similarity	NPC264245
0.5556	Remote Similarity	NPC603646
0.5484	Remote Similarity	NPC85095
0.5469	Remote Similarity	NPC473943
0.5385	Remote Similarity	NPC488870
0.5333	Remote Similarity	NPC600590
0.5323	Remote Similarity	NPC23852
0.5312	Remote Similarity	NPC19607
0.5294	Remote Similarity	NPC218186
0.5246	Remote Similarity	NPC154330
0.5231	Remote Similarity	NPC155011
0.5217	Remote Similarity	NPC489072
0.5179	Remote Similarity	NPC111234
0.5161	Remote Similarity	NPC113733
0.5152	Remote Similarity	NPC47761
0.5082	Remote Similarity	NPC221758
0.5079	Remote Similarity	NPC51014

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC87604 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7611
0.1-0.2	1395
0.2-0.3	113
0.3-0.4	26
0.4-0.5	2
0.5-0.6	2
0.6-0.7	1
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
0.6034	Remote Similarity	NPD6942	Phase 4
0.5932	Remote Similarity	NPD7339	Approved
0.5082	Remote Similarity	NPD4786	Phase 1

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