NPASS Compound

Natural Product: NPC591227

Natural Product ID	NPC591227
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	(2~{S},5~{R})-5-[(3~{S},8~{S},9~{S},10~{R},13~{R},14~{S},17~{R})-3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1~{H}-cyclopenta[a]phenanthren-17-yl]-2-isopropenyl-hexane-1,2-diol
IUPAC Name	(2~{S},5~{R})-5-[(3~{S},8~{S},9~{S},10~{R},13~{R},14~{S},17~{R})-3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1~{H}-cyclopenta[a]phenanthren-17-yl]-2-isopropenyl-hexane-1,2-diol
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 77 80 0 0 0 0 0 0 0 0999 V2000 -6.2807 2.0754 -0.2657 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2071 0.9001 0.3260 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1730 0.8366 1.8103 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1580 -0.3480 -0.4548 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.2976 -0.0338 -1.8038 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.3323 -1.2652 -0.1218 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2384 -1.6083 1.2151 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8454 -1.0503 -0.1854 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6665 -0.2027 -0.5704 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3501 -0.9291 -0.2909 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.3691 -2.1637 -1.0955 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2636 0.0379 -0.5393 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.4897 1.2137 0.4270 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1636 1.4131 1.1493 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7852 0.8697 0.1807 C 0 0 1 0 0 0 0 0 0 0 0 0 2.1543 0.5313 0.6650 C 0 0 2 0 0 0 0 0 0 0 0 0 2.7333 1.5513 1.5846 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1346 1.1630 1.8870 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8926 0.5115 1.0335 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2819 0.1654 1.4186 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1727 0.8667 0.4038 C 0 0 1 0 0 0 0 0 0 0 0 0 8.1818 0.0487 -0.0849 O 0 0 0 0 0 0 0 0 0 0 0 0 6.4189 1.5996 -0.6543 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2998 0.8614 -1.2987 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4416 0.0946 -0.3097 C 0 0 1 0 0 0 0 0 0 0 0 0 4.8090 -1.3817 -0.5155 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9861 0.3320 -0.5840 C 0 0 1 0 0 0 0 0 0 0 0 0 2.3667 -0.8532 -1.3154 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9130 -0.7194 -1.5524 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1243 -0.4183 -0.2962 C 0 0 2 0 0 0 0 0 0 0 0 0 0.2843 -1.4428 0.7755 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3156 2.9770 0.3223 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3049 2.1112 -1.3445 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7285 -0.0945 2.1575 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2071 0.9554 2.2386 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5975 1.7051 2.2032 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8346 -0.6974 -2.3675 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2621 -0.6695 -0.2748 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3726 -2.1321 -0.7853 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6544 -2.4673 1.4125 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7544 -1.3415 0.8782 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8086 -1.9674 -0.8309 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6997 -0.1098 -1.6963 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6870 0.8152 -0.1871 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3853 -1.1467 0.8180 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9923 -2.9271 -0.5415 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9291 -2.0303 -2.0677 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4344 -2.6431 -1.3346 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3490 0.4225 -1.5846 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2205 0.9527 1.2187 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7832 2.1144 -0.1397 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1544 0.9765 2.1519 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0222 2.5264 1.2209 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8530 1.5399 -0.6982 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2019 -0.4586 1.2080 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1661 1.5144 2.5392 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7678 2.5639 1.1458 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5756 1.4224 2.8613 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4722 0.4839 2.4540 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4642 -0.9376 1.4122 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7152 1.6617 0.9997 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1622 -0.8608 0.2938 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1100 2.6252 -0.2945 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1689 1.8292 -1.4688 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7158 0.2139 -2.0934 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6517 1.6087 -1.8153 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9166 -1.4395 -0.4818 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5399 -1.6557 -1.5556 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3394 -2.0261 0.2513 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8411 1.2226 -1.2163 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6352 -1.8042 -0.8417 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8478 -0.8669 -2.3401 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7622 0.1823 -2.2180 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5575 -1.5719 -2.1190 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3240 -0.9762 1.8050 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5953 -2.1473 0.8539 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1595 -2.1085 0.6151 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 0 2 4 1 0 4 5 1 6 4 6 1 0 6 7 1 0 4 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 10 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 2 0 19 20 1 0 20 21 1 0 21 22 1 0 21 23 1 0 23 24 1 0 24 25 1 0 25 26 1 1 25 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 1 1 30 12 1 0 30 15 1 0 27 16 1 0 25 19 1 0 1 32 1 0 1 33 1 0 3 34 1 0 3 35 1 0 3 36 1 0 5 37 1 0 6 38 1 0 6 39 1 0 7 40 1 0 8 41 1 0 8 42 1 0 9 43 1 0 9 44 1 0 10 45 1 1 11 46 1 0 11 47 1 0 11 48 1 0 12 49 1 6 13 50 1 0 13 51 1 0 14 52 1 0 14 53 1 0 15 54 1 6 16 55 1 1 17 56 1 0 17 57 1 0 18 58 1 0 20 59 1 0 20 60 1 0 21 61 1 1 22 62 1 0 23 63 1 0 23 64 1 0 24 65 1 0 24 66 1 0 26 67 1 0 26 68 1 0 26 69 1 0 27 70 1 6 28 71 1 0 28 72 1 0 29 73 1 0 29 74 1 0 31 75 1 0 31 76 1 0 31 77 1 0 M END

Standard InCHIKey	UKAKQBVHJAEXJL-MTITXHKXSA-N
Standard InCHI	InChI=1S/C28H46O3/c1-18(2)28(31,17-29)15-10-19(3)23-8-9-24-22-7-6-20-16-21(30)11-13-26(20,4)25(22)12-14-27(23,24)5/h6,19,21-25,29-31H,1,7-17H2,2-5H3/t19-,21+,22+,23-,24+,25+,26+,27-,28-/m1/s1
SMILES	C=C(C)[C@](O)(CO)CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	430.34	Volume:	479.716 ? Van der Waals volume.
Dense:	0.897	LogP:	5.336 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.383 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.031 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	21.0
TPSA:	60.69 ? Topological Polar Surface Area.	H-Bond Acceptor:	3.0
H-Bond Donor:	3.0	Rings:	4.0
Heavy Atoms:	3.0

MedChem Properties

QED Drug-Likeness Score:	0.478	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.729	Fsp³:	0.857
MCE-18:	74.731 ? 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:	0.658	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.004 ? 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:	0.526	Promiscuous compounds:	0.467

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.326	MDCK Permeability:	-5.136
Pgp-inhibitor:	0.001	Pgp-substrate:	0.126
PAMPA:	0.047 ? 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%):	0.016	30% Bioavailability (F30%):	0.45
50% Bioavailability (F50%):	0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.04	MRP1:	0.05
Plasma Protein Binding (PPB):	85.342%	Volume Distribution (VD):	-0.105
Fu:	15.963% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.848
BSEP inhibitor:	0.009

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.001
CYP2D6-inhibitor:	0.013	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.96	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.997
HLM stability:	0.019 ? 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):

12.075

Half-life (T1/2):

1.069

ADMET: Toxicity

hERG Blockers:	0.129	hERG Blockers (10um):	0.175
Human Hepatotoxicity (H-HT):	0.779	Drug-induced Liver Injury (DILI):	0.095
AMES Toxicity:	0.322	Rat Oral Acute Toxicity:	0.078
Maximum Recommended Daily Dose:	0.771	Skin Sensitization:	0.986
Carcinogencity:	0.934	Eye Corrosion:	0.008
Eye Irritation:	0.897	Respiratory Toxicity:	0.568
Drug-induced Neurotoxicity:	0.041	Ototoxicity:	0.634
Hematotoxicity:	0.296	Drug-induced Nephrotoxicity:	0.524
Genotoxicity:	0.142	RPMI-8226 Immunitoxicity:	0.069
A549 Cytotoxicity:	0.565	Hek293 Cytotoxicity:	0.668
BCF:	1.951 ? 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:	4.015 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.352 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.754 ? 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
NPO60497	Nephthea sp.	Genus	Nephtheidae	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 NPC591227 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	24028
0.1-0.2	21871
0.2-0.3	3602
0.3-0.4	225
0.4-0.5	75
0.5-0.6	19
0.6-0.7	16
0.7-0.8	2
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8462	Intermediate Similarity	NPC484739
0.8113	Intermediate Similarity	NPC241290
0.8113	Intermediate Similarity	NPC164840
0.8113	Intermediate Similarity	NPC209944
0.7778	Intermediate Similarity	NPC155986
0.7692	Intermediate Similarity	NPC162742
0.7692	Intermediate Similarity	NPC304309
0.7692	Intermediate Similarity	NPC470228
0.7593	Intermediate Similarity	NPC198968
0.7547	Intermediate Similarity	NPC22105
0.7547	Intermediate Similarity	NPC34019
0.7547	Intermediate Similarity	NPC107059
0.7407	Intermediate Similarity	NPC136188
0.7407	Intermediate Similarity	NPC28657
0.7407	Intermediate Similarity	NPC474216
0.7321	Intermediate Similarity	NPC321381
0.7273	Intermediate Similarity	NPC230301
0.7273	Intermediate Similarity	NPC285893
0.7273	Intermediate Similarity	NPC134847
0.7143	Intermediate Similarity	NPC264245
0.6897	Remote Similarity	NPC59453
0.6833	Remote Similarity	NPC488870
0.678	Remote Similarity	NPC603646
0.6667	Remote Similarity	NPC473943
0.661	Remote Similarity	NPC472265
0.6607	Remote Similarity	NPC600590
0.6491	Remote Similarity	NPC154330
0.6393	Remote Similarity	NPC240650
0.6393	Remote Similarity	NPC155011
0.6379	Remote Similarity	NPC113733
0.6333	Remote Similarity	NPC318495
0.6316	Remote Similarity	NPC221758
0.629	Remote Similarity	NPC47761
0.6271	Remote Similarity	NPC51014
0.6167	Remote Similarity	NPC328714
0.6066	Remote Similarity	NPC33913
0.5902	Remote Similarity	NPC87604
0.5873	Remote Similarity	NPC243985
0.5873	Remote Similarity	NPC280710
0.5806	Remote Similarity	NPC474634
0.5781	Remote Similarity	NPC474164
0.5714	Remote Similarity	NPC96319
0.5714	Remote Similarity	NPC477522
0.5667	Remote Similarity	NPC328313
0.5574	Remote Similarity	NPC76879
0.5556	Remote Similarity	NPC1272
0.5556	Remote Similarity	NPC470614
0.5522	Remote Similarity	NPC601043
0.5522	Remote Similarity	NPC605412
0.5246	Remote Similarity	NPC151519
0.5238	Remote Similarity	NPC317927
0.5161	Remote Similarity	NPC20688
0.5147	Remote Similarity	NPC474349
0.5147	Remote Similarity	NPC474189
0.5082	Remote Similarity	NPC81306

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC591227 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7673
0.1-0.2	1290
0.2-0.3	160
0.3-0.4	20
0.4-0.5	2
0.5-0.6	2
0.6-0.7	1
0.7-0.8	2
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
0.7407	Intermediate Similarity	NPD6942	Phase 4
0.7273	Intermediate Similarity	NPD7339	Approved
0.6316	Remote Similarity	NPD4786	Phase 1
0.5714	Remote Similarity	NPD3701	Pre-clinical
0.5246	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