NPASS Compound

Natural Product: NPC34019

Natural Product ID	NPC34019
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Petrosterol
IUPAC Name	(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R,5R)-5-[(1R,2R)-2-methylcyclopropyl]hexan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
Synonyms	Petrosterol
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL559744
PubChem CID	194249
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0003566] Cholestane steroids [CHEMONTID:0001469] Cholesterols 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 78 82 0 0 0 0 0 0 0 0999 V2000 -7.9272 -0.7423 1.9795 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.6956 -0.1444 1.7162 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.6222 -1.0960 2.2011 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2693 -0.5205 1.9471 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0487 -0.3768 0.4540 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1871 0.3352 -0.1914 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0154 1.2375 -1.1453 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7339 1.6709 -1.7038 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6764 0.6251 -1.2928 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.8203 0.4514 0.1721 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5818 -0.0115 0.8780 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4378 0.9114 0.4530 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1567 0.5586 -0.9835 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.3466 1.1523 -1.7152 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9353 0.8792 -3.1271 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5063 1.4252 -3.0774 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9649 1.2102 -1.6309 C 0 0 2 0 0 0 0 0 0 0 0 0 2.3335 0.6515 -1.5895 C 0 0 1 0 0 0 0 0 0 0 0 0 2.8534 0.5020 -0.1858 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2742 -0.0489 -0.1778 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8026 -0.1922 1.2253 C 0 0 2 0 0 0 0 0 0 0 0 0 6.2030 -0.7390 1.1422 C 0 0 2 0 0 0 0 0 0 0 0 0 6.9993 -0.9938 2.3713 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3333 0.1948 1.5300 C 0 0 1 0 0 0 0 0 0 0 0 0 8.5392 0.1606 0.6116 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9866 -1.1486 2.0558 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6348 -0.5815 -2.3426 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2230 -0.9398 -1.1798 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6094 0.0643 0.2194 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8490 -1.7526 -0.0920 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.1009 -1.3670 1.2054 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6377 0.7877 2.2790 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8416 -2.0618 1.7472 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8246 -1.2320 3.2950 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4878 -1.2301 2.3051 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1962 0.4385 2.4816 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9116 1.7283 -1.5814 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7469 1.7473 -2.8220 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4571 2.6440 -1.2494 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9110 -0.2472 -1.9247 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0542 1.4623 0.6436 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7414 0.1964 1.9736 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3383 -1.0645 0.7933 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3824 0.9494 1.1385 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9071 1.9446 0.4698 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2765 2.2734 -1.5902 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9619 -0.1803 -3.4238 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5363 1.4448 -3.8699 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3883 2.5080 -3.3197 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1582 0.9760 -3.8194 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0442 2.2606 -1.2056 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9955 1.4619 -2.0437 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1836 -0.1896 0.3751 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8708 1.4600 0.3492 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9695 0.5973 -0.7412 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2377 -1.0270 -0.6946 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8397 0.7681 1.7476 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3661 -1.4215 0.2730 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5139 -0.8197 3.3517 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7176 -1.8332 2.3404 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0820 1.1798 1.9673 H 0 0 0 0 0 0 0 0 0 0 0 0 9.4190 0.6342 1.0747 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7884 -0.8706 0.3348 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2387 0.6854 -0.3278 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1082 -0.6534 2.5021 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6278 -1.4715 2.9109 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7204 -2.0806 1.5092 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7457 -0.5604 -2.5922 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1694 -0.6680 -3.3433 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5472 -1.5186 -1.7539 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2121 -1.2489 -2.1525 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2861 -1.2303 -1.2321 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2491 -1.5196 -0.3900 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9605 -0.8036 -0.3483 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2692 0.9206 -0.0217 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9164 -1.7971 -1.2014 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6170 -2.5003 0.2700 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8909 -2.2140 0.2207 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 2 0 7 8 1 0 8 9 1 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 1 0 24 25 1 0 21 26 1 0 18 27 1 0 13 28 1 1 6 29 1 0 5 30 1 6 29 2 1 0 10 5 1 0 17 13 1 0 24 22 1 0 14 9 1 0 1 31 1 0 2 32 1 1 3 33 1 0 3 34 1 0 4 35 1 0 4 36 1 0 7 37 1 0 8 38 1 0 8 39 1 0 9 40 1 6 10 41 1 1 11 42 1 0 11 43 1 0 12 44 1 0 12 45 1 0 14 46 1 6 15 47 1 0 15 48 1 0 16 49 1 0 16 50 1 0 17 51 1 1 18 52 1 6 19 53 1 0 19 54 1 0 20 55 1 0 20 56 1 0 21 57 1 1 22 58 1 6 23 59 1 0 23 60 1 0 24 61 1 1 25 62 1 0 25 63 1 0 25 64 1 0 26 65 1 0 26 66 1 0 26 67 1 0 27 68 1 0 27 69 1 0 27 70 1 0 28 71 1 0 28 72 1 0 28 73 1 0 29 74 1 0 29 75 1 0 30 76 1 0 30 77 1 0 30 78 1 0 M END

Standard InCHIKey	AOOVLQXWRHMRMX-BFPAFGTMSA-N
Standard InCHI	InChI=1S/C29H48O/c1-18(24-16-20(24)3)6-7-19(2)25-10-11-26-23-9-8-21-17-22(30)12-14-28(21,4)27(23)13-15-29(25,26)5/h8,18-20,22-27,30H,6-7,9-17H2,1-5H3/t18-,19-,20-,22+,23+,24+,25-,26+,27+,28+,29-/m1/s1
SMILES	O[C@H]1CC[C@]2(C(=CC[C@@H]3[C@@H]2CC[C@]2([C@H]3CC[C@@H]2[C@@H](CC[C@H]([C@@H]2C[C@H]2C)C)C)C)C1)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	412.37	Volume:	473.512 ? Van der Waals volume.
Dense:	0.871	LogP:	7.767 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	5.333 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-6.96 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	23.0
TPSA:	20.23 ? Topological Polar Surface Area.	H-Bond Acceptor:	1.0
H-Bond Donor:	1.0	Rings:	5.0
Heavy Atoms:	1.0

MedChem Properties

QED Drug-Likeness Score:	0.46	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.583	Fsp³:	0.931
MCE-18:	81.929 ? 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:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.925	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:	0.54	Promiscuous compounds:	0.042

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.185	MDCK Permeability:	-4.992
Pgp-inhibitor:	0.017	Pgp-substrate:	0.125
PAMPA:	0.01 ? 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%):	0.015	30% Bioavailability (F30%):	0.299
50% Bioavailability (F50%):	0.985

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.079	MRP1:	0.142
Plasma Protein Binding (PPB):	95.866%	Volume Distribution (VD):	-0.139
Fu:	5.514% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.776
BSEP inhibitor:	0.059

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.001
CYP2C19-inhibitor:	0.206	CYP2C19-substrate:	0.088
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.184
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.646
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.791 ? 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):

15.382

Half-life (T1/2):

0.828

ADMET: Toxicity

hERG Blockers:	0.192	hERG Blockers (10um):	0.343
Human Hepatotoxicity (H-HT):	0.564	Drug-induced Liver Injury (DILI):	0.295
AMES Toxicity:	0.203	Rat Oral Acute Toxicity:	0.166
Maximum Recommended Daily Dose:	0.648	Skin Sensitization:	0.877
Carcinogencity:	0.868	Eye Corrosion:	0.143
Eye Irritation:	0.868	Respiratory Toxicity:	0.774
Drug-induced Neurotoxicity:	0.064	Ototoxicity:	0.498
Hematotoxicity:	0.344	Drug-induced Nephrotoxicity:	0.493
Genotoxicity:	0.029	RPMI-8226 Immunitoxicity:	0.048
A549 Cytotoxicity:	0.36	Hek293 Cytotoxicity:	0.682
BCF:	2.967 ? 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:	4.623 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.061 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.218 ? 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
NPO32556	Ianthella sp.	Species	Thorectidae	Eukaryota	n.a.	Vietnamese	n.a.	PMID[19615900]
NPO32556	Ianthella sp.	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[8254355]
NPO32556	Ianthella sp.	Species	Thorectidae	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

Activity Type	# Activity
Activity	3
IC50	6

Activity Type	# Activity
Cell line	9

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
NPT116	Cell line	HL-60	Homo sapiens	Activity	=	52.58	%	PMID[8246238]
NPT116	Cell line	HL-60	Homo sapiens	Activity	=	27.4	%	PMID[8246238]
NPT116	Cell line	HL-60	Homo sapiens	Activity	=	12.61	%	PMID[8246238]
NPT466	Cell line	U-937	Homo sapiens	IC50	=	18700.0	nM	PMID[23122818]
NPT146	Cell line	SK-OV-3	Homo sapiens	IC50	=	19800.0	nM	PMID[23122818]
NPT83	Cell line	MCF7	Homo sapiens	IC50	=	16400.0	nM	PMID[23122818]
NPT139	Cell line	HT-29	Homo sapiens	IC50	=	46500.0	nM	PMID[23122818]
NPT116	Cell line	HL-60	Homo sapiens	IC50	=	21500.0	nM	PMID[23122818]
NPT81	Cell line	A549	Homo sapiens	IC50	=	11500.0	nM	PMID[25237727]

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 NPC34019 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	24029
0.1-0.2	21711
0.2-0.3	3720
0.3-0.4	233
0.4-0.5	77
0.5-0.6	39
0.6-0.7	16
0.7-0.8	0
0.8-0.85	9
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8913	High Similarity	NPC162742
0.8913	High Similarity	NPC304309
0.8913	High Similarity	NPC470228
0.8367	Intermediate Similarity	NPC230301
0.8367	Intermediate Similarity	NPC198968
0.8367	Intermediate Similarity	NPC285893
0.8333	Intermediate Similarity	NPC22105
0.8333	Intermediate Similarity	NPC107059
0.8163	Intermediate Similarity	NPC136188
0.8163	Intermediate Similarity	NPC28657
0.8163	Intermediate Similarity	NPC474216
0.8	Intermediate Similarity	NPC134847
0.7843	Intermediate Similarity	NPC241290
0.7843	Intermediate Similarity	NPC164840
0.7843	Intermediate Similarity	NPC484739
0.7843	Intermediate Similarity	NPC209944
0.7843	Intermediate Similarity	NPC155986
0.7692	Intermediate Similarity	NPC321381
0.7547	Intermediate Similarity	NPC59453
0.75	Intermediate Similarity	NPC264245
0.7407	Intermediate Similarity	NPC603646
0.7273	Intermediate Similarity	NPC473943
0.7255	Intermediate Similarity	NPC600590
0.7222	Intermediate Similarity	NPC472265
0.7143	Intermediate Similarity	NPC488870
0.7115	Intermediate Similarity	NPC154330
0.6981	Remote Similarity	NPC113733
0.6964	Remote Similarity	NPC155011
0.6923	Remote Similarity	NPC221758
0.6852	Remote Similarity	NPC51014
0.6842	Remote Similarity	NPC47761
0.6607	Remote Similarity	NPC33913
0.6481	Remote Similarity	NPC328313
0.6429	Remote Similarity	NPC328714
0.6379	Remote Similarity	NPC243985
0.6379	Remote Similarity	NPC280710
0.6379	Remote Similarity	NPC240650
0.6316	Remote Similarity	NPC318495
0.6275	Remote Similarity	NPC96319
0.6271	Remote Similarity	NPC474164
0.6207	Remote Similarity	NPC477522
0.614	Remote Similarity	NPC87604
0.5968	Remote Similarity	NPC601043
0.5968	Remote Similarity	NPC605412
0.5818	Remote Similarity	NPC81306
0.5763	Remote Similarity	NPC1272
0.5763	Remote Similarity	NPC470614
0.5714	Remote Similarity	NPC151519
0.5667	Remote Similarity	NPC474752
0.5667	Remote Similarity	NPC474683
0.5614	Remote Similarity	NPC20688
0.5593	Remote Similarity	NPC31564
0.5593	Remote Similarity	NPC145879
0.5517	Remote Similarity	NPC76879
0.5517	Remote Similarity	NPC28862
0.5345	Remote Similarity	NPC109546
0.5345	Remote Similarity	NPC317458
0.5345	Remote Similarity	NPC47982
0.5333	Remote Similarity	NPC26959
0.5254	Remote Similarity	NPC84694
0.5254	Remote Similarity	NPC143182
0.5231	Remote Similarity	NPC176012
0.5167	Remote Similarity	NPC317927
0.5161	Remote Similarity	NPC44083
0.5152	Remote Similarity	NPC5985
0.5147	Remote Similarity	NPC235126
0.5147	Remote Similarity	NPC309493
0.5147	Remote Similarity	NPC242419
0.5085	Remote Similarity	NPC247325
0.5085	Remote Similarity	NPC189972
0.5079	Remote Similarity	NPC475789
0.5079	Remote Similarity	NPC268406
0.5077	Remote Similarity	NPC474970
0.5077	Remote Similarity	NPC474349
0.5077	Remote Similarity	NPC474189
0.5075	Remote Similarity	NPC91604
0.5072	Remote Similarity	NPC147835
0.5072	Remote Similarity	NPC253645
0.5072	Remote Similarity	NPC85001
0.5072	Remote Similarity	NPC95920
0.507	Remote Similarity	NPC3715

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC34019 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7738
0.1-0.2	1239
0.2-0.3	134
0.3-0.4	32
0.4-0.5	2
0.5-0.6	1
0.6-0.7	2
0.7-0.8	0
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8367	Intermediate Similarity	NPD7339	Approved
0.8163	Intermediate Similarity	NPD6942	Phase 4
0.6923	Remote Similarity	NPD4786	Phase 1
0.6275	Remote Similarity	NPD3701	Pre-clinical
0.5714	Remote Similarity	NPD3667	Phase 4

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