NPASS Compound

Structure

NPC66105 OpenBabel07101719512D 33 36 0 0 1 0 0 0 0 0999 V2000 -2.5279 2.4324 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3705 0.9730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5516 1.6912 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8285 1.0402 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1321 -2.3483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3561 2.3021 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8426 -1.4595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.9730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6852 0.9730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8426 1.4595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0251 -0.9730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6852 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8426 3.1447 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4532 -1.7601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3291 2.3021 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8426 -0.4865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6852 -1.9459 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8426 -1.4595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5279 1.4595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6852 0.9730 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4532 -0.1858 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6852 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 0.9730 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.1304 3.1447 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5279 -0.4865 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.7539 0.7395 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5279 -1.4595 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8426 1.4595 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8426 -0.4865 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6168 2.3021 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6168 3.9873 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7056 0.9418 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 2 0 0 0 0 2 19 1 0 0 0 0 3 26 1 0 0 0 0 4 26 1 0 0 0 0 7 29 1 0 0 0 0 9 10 1 0 0 0 0 9 22 1 0 0 0 0 10 23 1 0 0 0 0 11 14 1 0 0 0 0 11 21 1 0 0 0 0 12 16 1 0 0 0 0 12 20 1 0 0 0 0 13 15 1 0 0 0 0 13 24 1 0 0 0 0 14 27 1 0 0 0 0 15 28 1 0 0 0 0 16 30 1 0 0 0 0 17 18 1 0 0 0 0 17 27 1 0 0 0 0 18 29 1 0 0 0 0 19 20 1 0 0 0 0 20 28 1 1 0 0 0 21 25 1 0 0 0 0 21 26 1 6 0 0 0 22 25 1 0 0 0 0 22 29 1 6 0 0 0 23 28 1 1 0 0 0 23 30 1 0 0 0 0 24 31 2 0 0 0 0 24 32 1 0 0 0 0 25 27 1 1 0 0 0 26 33 1 0 0 0 0 27 5 1 1 0 0 0 28 6 1 1 0 0 0 29 30 1 1 0 0 0 30 8 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	458.38
Volume:	514.308
LogP:	6.541
LogD:	4.936
LogS:	-4.603
# Rotatable Bonds:	5
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.42
Synthetic Accessibility Score:	4.858
Fsp3:	0.9
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.239
MDCK Permeability:	1.405596049153246e-05
Pgp-inhibitor:	0.15
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.269
30% Bioavailability (F30%):	0.818

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.02
Plasma Protein Binding (PPB):	95.4782485961914%
Volume Distribution (VD):	0.717
Pgp-substrate:	2.3640012741088867%

ADMET: Metabolism

CYP1A2-inhibitor:	0.021
CYP1A2-substrate:	0.391
CYP2C19-inhibitor:	0.031
CYP2C19-substrate:	0.928
CYP2C9-inhibitor:	0.156
CYP2C9-substrate:	0.832
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.583
CYP3A4-inhibitor:	0.146
CYP3A4-substrate:	0.179

ADMET: Excretion

Clearance (CL):	2.853
Half-life (T1/2):	0.266

ADMET: Toxicity

hERG Blockers:	0.09
Human Hepatotoxicity (H-HT):	0.209
Drug-inuced Liver Injury (DILI):	0.02
AMES Toxicity:	0.002
Rat Oral Acute Toxicity:	0.052
Maximum Recommended Daily Dose:	0.026
Skin Sensitization:	0.529
Carcinogencity:	0.027
Eye Corrosion:	0.605
Eye Irritation:	0.32
Respiratory Toxicity:	0.864

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC66105

Natural Product ID:	NPC66105
*Common Name:**	Dysoxyhainic Acid H
IUPAC Name:	3-[(3S,4S,5R,8R,9R,10R,13R,14S,15R)-15-(2-hydroxypropan-2-yl)-4,9,10,13-tetramethyl-3-prop-1-en-2-yl-2,3,5,6,7,8,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-4-yl]propanoic acid
Synonyms:	Dysoxyhainic Acid H
Standard InCHIKey:	OJFLQTYBOGSXCL-FBJARBBYSA-N
Standard InCHI:	InChI=1S/C30H50O3/c1-19(2)20-12-16-30(8)23(28(20,6)15-13-24(31)32)10-9-22-25-21(26(3,4)33)11-14-27(25,5)17-18-29(22,30)7/h20-23,25,33H,1,9-18H2,2-8H3,(H,31,32)/t20-,21+,22+,23+,25+,27+,28-,29+,30+/m0/s1
SMILES:	C=C(C)[C@@H]1CC[C@]2(C)[C@H](CC[C@@H]3[C@H]4[C@@H](CC[C@]4(C)CC[C@@]23C)C(C)(C)O)[C@@]1(C)CCC(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1642041
PubChem CID:	50942506
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0003364] Steroid acids

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO144	Dysoxylum hainanense	Species	Meliaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[18771268]
NPO144	Dysoxylum hainanense	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21131198]
NPO144	Dysoxylum hainanense	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO144	Dysoxylum hainanense	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO144	Dysoxylum hainanense	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO144	Dysoxylum hainanense	Species	Meliaceae	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	NP ID	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
MIC	11

Activity Type	# Activity
Organism	11

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	=	3.12	ug.mL-1	PMID[516751]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	3.12	ug.mL-1	PMID[516751]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	50.0	ug.mL-1	PMID[516751]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	MIC	>	50.0	ug.mL-1	PMID[516751]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	50.0	ug.mL-1	PMID[516751]
NPT2909	Organism	Shigella flexneri	Shigella flexneri	MIC	>	50.0	ug.mL-1	PMID[516751]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	50.0	ug.mL-1	PMID[516751]
NPT20	Organism	Candida albicans	Candida albicans	MIC	>	50.0	ug.mL-1	PMID[516751]
NPT1533	Organism	Saccharomyces	Saccharomyces	MIC	>	50.0	ug.mL-1	PMID[516751]
NPT327	Organism	Microsporum gypseum	Microsporum gypseum	MIC	>	50.0	ug.mL-1	PMID[516751]
NPT329	Organism	Trichophyton rubrum	Trichophyton rubrum	MIC	>	50.0	ug.mL-1	PMID[516751]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC66105 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	152
0.1-0.2	1596
0.2-0.3	9418
0.3-0.4	14108
0.4-0.5	5931
0.5-0.6	6171
0.6-0.7	3761
0.7-0.8	1370
0.8-0.85	137
0.85-0.9	39
0.9-0.95	8
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9583	High Similarity	NPC246445
0.9459	High Similarity	NPC192744
0.9452	High Similarity	NPC68828
0.9437	High Similarity	NPC330659
0.9437	High Similarity	NPC244708
0.9437	High Similarity	NPC161187
0.9324	High Similarity	NPC321690
0.9189	High Similarity	NPC212661
0.9189	High Similarity	NPC471035
0.9054	High Similarity	NPC20466
0.8974	High Similarity	NPC245866
0.8974	High Similarity	NPC472740
0.8961	High Similarity	NPC147066
0.8961	High Similarity	NPC232625
0.8947	High Similarity	NPC215843
0.8904	High Similarity	NPC36310
0.8904	High Similarity	NPC279241
0.8816	High Similarity	NPC63020
0.875	High Similarity	NPC201655
0.875	High Similarity	NPC294438
0.875	High Similarity	NPC264317
0.8734	High Similarity	NPC167103
0.8734	High Similarity	NPC471037
0.8718	High Similarity	NPC201912
0.8718	High Similarity	NPC38350
0.8701	High Similarity	NPC231431
0.8701	High Similarity	NPC477371
0.8701	High Similarity	NPC158846
0.8701	High Similarity	NPC201459
0.8642	High Similarity	NPC80590
0.8642	High Similarity	NPC70661
0.8642	High Similarity	NPC12774
0.8642	High Similarity	NPC2783
0.8625	High Similarity	NPC263974
0.8611	High Similarity	NPC290445
0.8611	High Similarity	NPC36616
0.8608	High Similarity	NPC260956
0.8608	High Similarity	NPC170985
0.8608	High Similarity	NPC145143
0.8608	High Similarity	NPC320514
0.8592	High Similarity	NPC42060
0.859	High Similarity	NPC37038
0.8553	High Similarity	NPC89294
0.8553	High Similarity	NPC104806
0.8537	High Similarity	NPC33768
0.8537	High Similarity	NPC136948
0.8537	High Similarity	NPC269360
0.8537	High Similarity	NPC134197
0.8537	High Similarity	NPC264005
0.8533	High Similarity	NPC46610
0.8533	High Similarity	NPC255168
0.8533	High Similarity	NPC18819
0.8519	High Similarity	NPC269638
0.8519	High Similarity	NPC29447
0.85	High Similarity	NPC477852
0.85	High Similarity	NPC69279
0.85	High Similarity	NPC477373
0.85	High Similarity	NPC83569
0.8493	Intermediate Similarity	NPC196197
0.8481	Intermediate Similarity	NPC142244
0.8481	Intermediate Similarity	NPC474484
0.8481	Intermediate Similarity	NPC477372
0.8481	Intermediate Similarity	NPC103754
0.8462	Intermediate Similarity	NPC471475
0.8462	Intermediate Similarity	NPC118987
0.8442	Intermediate Similarity	NPC106078
0.8442	Intermediate Similarity	NPC471897
0.8442	Intermediate Similarity	NPC107039
0.8442	Intermediate Similarity	NPC471899
0.8442	Intermediate Similarity	NPC238227
0.8434	Intermediate Similarity	NPC4309
0.8434	Intermediate Similarity	NPC183374
0.8434	Intermediate Similarity	NPC16377
0.8434	Intermediate Similarity	NPC471900
0.8434	Intermediate Similarity	NPC211162
0.8434	Intermediate Similarity	NPC474719
0.8434	Intermediate Similarity	NPC146937
0.8434	Intermediate Similarity	NPC255176
0.8415	Intermediate Similarity	NPC155011
0.8415	Intermediate Similarity	NPC475007
0.8415	Intermediate Similarity	NPC472505
0.8378	Intermediate Similarity	NPC91369
0.8378	Intermediate Similarity	NPC108131
0.8375	Intermediate Similarity	NPC477858
0.8375	Intermediate Similarity	NPC133391
0.8354	Intermediate Similarity	NPC170038
0.8354	Intermediate Similarity	NPC206735
0.8333	Intermediate Similarity	NPC24772
0.8333	Intermediate Similarity	NPC271974
0.8333	Intermediate Similarity	NPC103734
0.8333	Intermediate Similarity	NPC213832
0.8333	Intermediate Similarity	NPC280654
0.8333	Intermediate Similarity	NPC110094
0.8333	Intermediate Similarity	NPC260385
0.8333	Intermediate Similarity	NPC220498
0.8333	Intermediate Similarity	NPC116146
0.8333	Intermediate Similarity	NPC262043
0.8333	Intermediate Similarity	NPC268736
0.8333	Intermediate Similarity	NPC57954
0.8333	Intermediate Similarity	NPC477931
0.8333	Intermediate Similarity	NPC247312
0.8313	Intermediate Similarity	NPC142361
0.8313	Intermediate Similarity	NPC128644
0.8313	Intermediate Similarity	NPC96496
0.8313	Intermediate Similarity	NPC474684
0.8272	Intermediate Similarity	NPC475726
0.8272	Intermediate Similarity	NPC470015
0.8272	Intermediate Similarity	NPC472743
0.8272	Intermediate Similarity	NPC168188
0.8272	Intermediate Similarity	NPC175410
0.8267	Intermediate Similarity	NPC72343
0.825	Intermediate Similarity	NPC263272
0.825	Intermediate Similarity	NPC164210
0.825	Intermediate Similarity	NPC267691
0.825	Intermediate Similarity	NPC471898
0.825	Intermediate Similarity	NPC162632
0.825	Intermediate Similarity	NPC274050
0.8243	Intermediate Similarity	NPC476734
0.8243	Intermediate Similarity	NPC252032
0.8243	Intermediate Similarity	NPC469941
0.8243	Intermediate Similarity	NPC319671
0.8243	Intermediate Similarity	NPC474962
0.8235	Intermediate Similarity	NPC169933
0.8228	Intermediate Similarity	NPC199595
0.8228	Intermediate Similarity	NPC16394
0.8219	Intermediate Similarity	NPC130459
0.8219	Intermediate Similarity	NPC474221
0.8219	Intermediate Similarity	NPC478180
0.8214	Intermediate Similarity	NPC254572
0.8214	Intermediate Similarity	NPC117122
0.8214	Intermediate Similarity	NPC229407
0.8214	Intermediate Similarity	NPC48824
0.8214	Intermediate Similarity	NPC250687
0.8193	Intermediate Similarity	NPC28252
0.8193	Intermediate Similarity	NPC472869
0.8193	Intermediate Similarity	NPC55309
0.8182	Intermediate Similarity	NPC39362
0.8182	Intermediate Similarity	NPC192540
0.8182	Intermediate Similarity	NPC201027
0.8182	Intermediate Similarity	NPC279666
0.8171	Intermediate Similarity	NPC474233
0.8171	Intermediate Similarity	NPC264665
0.8171	Intermediate Similarity	NPC474482
0.8171	Intermediate Similarity	NPC74595
0.8171	Intermediate Similarity	NPC475745
0.8171	Intermediate Similarity	NPC475509
0.8171	Intermediate Similarity	NPC156981
0.8171	Intermediate Similarity	NPC194937
0.8171	Intermediate Similarity	NPC476038
0.8171	Intermediate Similarity	NPC165064
0.8148	Intermediate Similarity	NPC258153
0.8148	Intermediate Similarity	NPC476458
0.8148	Intermediate Similarity	NPC193347
0.8148	Intermediate Similarity	NPC474605
0.8148	Intermediate Similarity	NPC251779
0.8148	Intermediate Similarity	NPC476292
0.8148	Intermediate Similarity	NPC69101
0.814	Intermediate Similarity	NPC160506
0.814	Intermediate Similarity	NPC475416
0.814	Intermediate Similarity	NPC471901
0.8133	Intermediate Similarity	NPC477929
0.8133	Intermediate Similarity	NPC235586
0.8125	Intermediate Similarity	NPC164999
0.8125	Intermediate Similarity	NPC104545
0.8118	Intermediate Similarity	NPC215029
0.8118	Intermediate Similarity	NPC269267
0.8118	Intermediate Similarity	NPC475921
0.8118	Intermediate Similarity	NPC476733
0.8118	Intermediate Similarity	NPC474570
0.8118	Intermediate Similarity	NPC474704
0.8108	Intermediate Similarity	NPC473225
0.8101	Intermediate Similarity	NPC476810
0.8101	Intermediate Similarity	NPC179028
0.8101	Intermediate Similarity	NPC321514
0.8095	Intermediate Similarity	NPC187376
0.8095	Intermediate Similarity	NPC159046
0.8095	Intermediate Similarity	NPC233836
0.8077	Intermediate Similarity	NPC69143
0.8077	Intermediate Similarity	NPC476601
0.8072	Intermediate Similarity	NPC94531
0.8072	Intermediate Similarity	NPC98270
0.8072	Intermediate Similarity	NPC311702
0.8072	Intermediate Similarity	NPC76518
0.8072	Intermediate Similarity	NPC292553
0.8072	Intermediate Similarity	NPC123319
0.8072	Intermediate Similarity	NPC283733
0.8068	Intermediate Similarity	NPC279974
0.8052	Intermediate Similarity	NPC103958
0.8052	Intermediate Similarity	NPC280026
0.8052	Intermediate Similarity	NPC167702
0.8052	Intermediate Similarity	NPC161923
0.8052	Intermediate Similarity	NPC183503
0.8052	Intermediate Similarity	NPC283908
0.8052	Intermediate Similarity	NPC162164
0.8052	Intermediate Similarity	NPC241854
0.8052	Intermediate Similarity	NPC251970
0.8052	Intermediate Similarity	NPC476046
0.8049	Intermediate Similarity	NPC310470
0.8049	Intermediate Similarity	NPC215893
0.8049	Intermediate Similarity	NPC170862

Chemically structural similarity: II. Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC66105 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	155
0.1-0.2	2054
0.2-0.3	4277
0.3-0.4	1746
0.4-0.5	485
0.5-0.6	165
0.6-0.7	164
0.7-0.8	93
0.8-0.85	8
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.875	High Similarity	NPD7520	Clinical (unspecified phase)
0.85	High Similarity	NPD4788	Approved
0.8333	Intermediate Similarity	NPD4224	Phase 2
0.8267	Intermediate Similarity	NPD6081	Approved
0.8148	Intermediate Similarity	NPD4221	Approved
0.8148	Intermediate Similarity	NPD4223	Phase 3
0.814	Intermediate Similarity	NPD8034	Phase 2
0.814	Intermediate Similarity	NPD8035	Phase 2
0.8108	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.8108	Intermediate Similarity	NPD5360	Phase 3
0.8072	Intermediate Similarity	NPD5329	Approved
0.8052	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7976	Intermediate Similarity	NPD6098	Approved
0.7952	Intermediate Similarity	NPD4197	Approved
0.7952	Intermediate Similarity	NPD4786	Approved
0.7848	Intermediate Similarity	NPD6117	Approved
0.7841	Intermediate Similarity	NPD6399	Phase 3
0.7765	Intermediate Similarity	NPD5205	Approved
0.7765	Intermediate Similarity	NPD4693	Phase 3
0.7765	Intermediate Similarity	NPD4138	Approved
0.7765	Intermediate Similarity	NPD4688	Approved
0.7765	Intermediate Similarity	NPD4690	Approved
0.7765	Intermediate Similarity	NPD4689	Approved
0.775	Intermediate Similarity	NPD6116	Phase 1
0.7727	Intermediate Similarity	NPD5284	Approved
0.7727	Intermediate Similarity	NPD5281	Approved
0.7722	Intermediate Similarity	NPD3702	Approved
0.7711	Intermediate Similarity	NPD3667	Approved
0.7701	Intermediate Similarity	NPD6673	Approved
0.7701	Intermediate Similarity	NPD6904	Approved
0.7701	Intermediate Similarity	NPD6080	Approved
0.7692	Intermediate Similarity	NPD6084	Phase 2
0.7692	Intermediate Similarity	NPD6083	Phase 2
0.7662	Intermediate Similarity	NPD4789	Approved
0.7654	Intermediate Similarity	NPD6118	Approved
0.7654	Intermediate Similarity	NPD3617	Approved
0.7654	Intermediate Similarity	NPD6115	Approved
0.7654	Intermediate Similarity	NPD6114	Approved
0.7654	Intermediate Similarity	NPD6697	Approved
0.759	Intermediate Similarity	NPD4139	Approved
0.759	Intermediate Similarity	NPD4692	Approved
0.7586	Intermediate Similarity	NPD5208	Approved
0.7586	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD5737	Approved
0.7586	Intermediate Similarity	NPD6672	Approved
0.7564	Intermediate Similarity	NPD4243	Approved
0.7564	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD4758	Discontinued
0.7564	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7558	Intermediate Similarity	NPD6409	Approved
0.7558	Intermediate Similarity	NPD5690	Phase 2
0.7558	Intermediate Similarity	NPD5280	Approved
0.7558	Intermediate Similarity	NPD6684	Approved
0.7558	Intermediate Similarity	NPD7146	Approved
0.7558	Intermediate Similarity	NPD7521	Approved
0.7558	Intermediate Similarity	NPD7334	Approved
0.7558	Intermediate Similarity	NPD4694	Approved
0.7558	Intermediate Similarity	NPD5330	Approved
0.7529	Intermediate Similarity	NPD3666	Approved
0.7529	Intermediate Similarity	NPD3665	Phase 1
0.7529	Intermediate Similarity	NPD3133	Approved
0.75	Intermediate Similarity	NPD4753	Phase 2
0.75	Intermediate Similarity	NPD5328	Approved
0.7473	Intermediate Similarity	NPD5695	Phase 3
0.7467	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD4245	Approved
0.7436	Intermediate Similarity	NPD4244	Approved
0.7419	Intermediate Similarity	NPD5696	Approved
0.7386	Intermediate Similarity	NPD6903	Approved
0.7375	Intermediate Similarity	NPD4784	Approved
0.7375	Intermediate Similarity	NPD4785	Approved
0.7356	Intermediate Similarity	NPD3618	Phase 1
0.7356	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD4195	Approved
0.7342	Intermediate Similarity	NPD5777	Approved
0.7333	Intermediate Similarity	NPD7515	Phase 2
0.7333	Intermediate Similarity	NPD6079	Approved
0.7333	Intermediate Similarity	NPD5693	Phase 1
0.7333	Intermediate Similarity	NPD6050	Approved
0.7308	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD3698	Phase 2
0.7303	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD7525	Registered
0.7253	Intermediate Similarity	NPD4202	Approved
0.7229	Intermediate Similarity	NPD5364	Discontinued
0.7222	Intermediate Similarity	NPD5692	Phase 3
0.7222	Intermediate Similarity	NPD5207	Approved
0.7215	Intermediate Similarity	NPD4747	Approved
0.7174	Intermediate Similarity	NPD7748	Approved
0.7174	Intermediate Similarity	NPD6001	Approved
0.7159	Intermediate Similarity	NPD4623	Approved
0.7159	Intermediate Similarity	NPD4519	Discontinued
0.7159	Intermediate Similarity	NPD5279	Phase 3
0.7143	Intermediate Similarity	NPD6402	Approved
0.7143	Intermediate Similarity	NPD7128	Approved
0.7143	Intermediate Similarity	NPD5739	Approved
0.7143	Intermediate Similarity	NPD6675	Approved
0.7143	Intermediate Similarity	NPD5694	Approved
0.7126	Intermediate Similarity	NPD3668	Phase 3
0.7097	Intermediate Similarity	NPD4629	Approved
0.7097	Intermediate Similarity	NPD5210	Approved
0.7089	Intermediate Similarity	NPD4137	Phase 3
0.7073	Intermediate Similarity	NPD6942	Approved
0.7073	Intermediate Similarity	NPD4190	Phase 3
0.7073	Intermediate Similarity	NPD7339	Approved
0.7073	Intermediate Similarity	NPD5275	Approved
0.7059	Intermediate Similarity	NPD4695	Discontinued
0.7053	Intermediate Similarity	NPD7638	Approved
0.7033	Intermediate Similarity	NPD4096	Approved
0.7	Intermediate Similarity	NPD6899	Approved
0.7	Intermediate Similarity	NPD4691	Approved
0.7	Intermediate Similarity	NPD6881	Approved
0.7	Intermediate Similarity	NPD7320	Approved
0.6979	Remote Similarity	NPD7640	Approved
0.6979	Remote Similarity	NPD6404	Discontinued
0.6979	Remote Similarity	NPD7639	Approved
0.6962	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD6926	Approved
0.6951	Remote Similarity	NPD5733	Approved
0.6951	Remote Similarity	NPD6924	Approved
0.6947	Remote Similarity	NPD4755	Approved
0.6947	Remote Similarity	NPD7902	Approved
0.6931	Remote Similarity	NPD6373	Approved
0.6931	Remote Similarity	NPD6372	Approved
0.69	Remote Similarity	NPD5697	Approved
0.69	Remote Similarity	NPD5701	Approved
0.6889	Remote Similarity	NPD3573	Approved
0.6882	Remote Similarity	NPD5133	Approved
0.6867	Remote Similarity	NPD3703	Phase 2
0.6863	Remote Similarity	NPD7102	Approved
0.6863	Remote Similarity	NPD7290	Approved
0.6863	Remote Similarity	NPD6883	Approved
0.6842	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD5222	Approved
0.6842	Remote Similarity	NPD7614	Phase 1
0.6842	Remote Similarity	NPD5221	Approved
0.6842	Remote Similarity	NPD4697	Phase 3
0.6832	Remote Similarity	NPD6011	Approved
0.6824	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD4518	Approved
0.6804	Remote Similarity	NPD5286	Approved
0.6804	Remote Similarity	NPD4700	Approved
0.6804	Remote Similarity	NPD4696	Approved
0.6804	Remote Similarity	NPD5285	Approved
0.6796	Remote Similarity	NPD6847	Approved
0.6796	Remote Similarity	NPD6617	Approved
0.6796	Remote Similarity	NPD6650	Approved
0.6796	Remote Similarity	NPD6869	Approved
0.6796	Remote Similarity	NPD8130	Phase 1
0.6796	Remote Similarity	NPD6649	Approved
0.6796	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD6933	Approved
0.6771	Remote Similarity	NPD5173	Approved
0.6768	Remote Similarity	NPD6052	Approved
0.6765	Remote Similarity	NPD6013	Approved
0.6765	Remote Similarity	NPD6014	Approved
0.6765	Remote Similarity	NPD6012	Approved
0.6747	Remote Similarity	NPD4058	Approved
0.6747	Remote Similarity	NPD4687	Approved
0.6739	Remote Similarity	NPD6051	Approved
0.6737	Remote Similarity	NPD5654	Approved
0.6735	Remote Similarity	NPD5223	Approved
0.6731	Remote Similarity	NPD8297	Approved
0.6731	Remote Similarity	NPD6882	Approved
0.6707	Remote Similarity	NPD5276	Approved
0.6705	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5225	Approved
0.6667	Remote Similarity	NPD5224	Approved
0.6667	Remote Similarity	NPD5211	Phase 2
0.6667	Remote Similarity	NPD4633	Approved
0.6667	Remote Similarity	NPD5226	Approved
0.6667	Remote Similarity	NPD8133	Approved
0.6667	Remote Similarity	NPD5091	Approved
0.6632	Remote Similarity	NPD7900	Approved
0.6632	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6628	Remote Similarity	NPD3671	Phase 1
0.66	Remote Similarity	NPD4754	Approved
0.66	Remote Similarity	NPD5174	Approved
0.66	Remote Similarity	NPD5175	Approved
0.6598	Remote Similarity	NPD5959	Approved
0.6569	Remote Similarity	NPD6614	Approved
0.6535	Remote Similarity	NPD5141	Approved
0.6509	Remote Similarity	NPD4632	Approved
0.65	Remote Similarity	NPD7632	Discontinued
0.6481	Remote Similarity	NPD7115	Discovery
0.6477	Remote Similarity	NPD6931	Approved
0.6477	Remote Similarity	NPD6930	Phase 2
0.6471	Remote Similarity	NPD4767	Approved
0.6471	Remote Similarity	NPD6008	Approved
0.6471	Remote Similarity	NPD4768	Approved
0.6463	Remote Similarity	NPD6923	Approved
0.6463	Remote Similarity	NPD6922	Approved
0.6463	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD5707	Approved
0.6444	Remote Similarity	NPD5362	Discontinued
0.6422	Remote Similarity	NPD6335	Approved
0.6421	Remote Similarity	NPD7637	Suspended

Bioactivity similarity: Similar Natural Products in NPASS

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