NPASS Compound

Structure

NPC202118 OpenBabel07101719132D 21 23 0 0 1 0 0 0 0 0999 V2000 4.6888 4.2247 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2575 2.3912 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7229 3.9659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 2 0 0 0 0 2 18 1 0 0 0 0 3 18 1 0 0 0 0 6 19 1 0 0 0 0 7 8 1 0 0 0 0 7 14 1 0 0 0 0 8 16 1 0 0 0 0 9 11 1 0 0 0 0 9 15 1 0 0 0 0 10 12 1 0 0 0 0 10 17 1 0 0 0 0 11 19 1 0 0 0 0 12 20 1 0 0 0 0 13 14 2 0 0 0 0 13 19 1 0 0 0 0 14 15 1 0 0 0 0 15 20 1 1 0 0 0 16 18 1 0 0 0 0 16 20 1 1 0 0 0 17 18 1 0 0 0 0 17 21 2 0 0 0 0 19 4 1 1 0 0 0 20 5 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	286.23
Volume:	329.688
LogP:	4.41
LogD:	4.352
LogS:	-5.155
# Rotatable Bonds:	1
TPSA:	17.07
# H-Bond Aceptor:	1
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.596
Synthetic Accessibility Score:	4.304
Fsp3:	0.75
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:	-4.863
MDCK Permeability:	1.8417984392726794e-05
Pgp-inhibitor:	0.956
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.705
30% Bioavailability (F30%):	0.089

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.036
Plasma Protein Binding (PPB):	94.42015838623047%
Volume Distribution (VD):	1.05
Pgp-substrate:	4.052339553833008%

ADMET: Metabolism

CYP1A2-inhibitor:	0.209
CYP1A2-substrate:	0.716
CYP2C19-inhibitor:	0.504
CYP2C19-substrate:	0.874
CYP2C9-inhibitor:	0.407
CYP2C9-substrate:	0.802
CYP2D6-inhibitor:	0.267
CYP2D6-substrate:	0.679
CYP3A4-inhibitor:	0.913
CYP3A4-substrate:	0.586

ADMET: Excretion

Clearance (CL):	2.795
Half-life (T1/2):	0.68

ADMET: Toxicity

hERG Blockers:	0.002
Human Hepatotoxicity (H-HT):	0.122
Drug-inuced Liver Injury (DILI):	0.045
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.03
Maximum Recommended Daily Dose:	0.898
Skin Sensitization:	0.055
Carcinogencity:	0.082
Eye Corrosion:	0.257
Eye Irritation:	0.952
Respiratory Toxicity:	0.958

Download Data

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

Natural Product: NPC202118

Natural Product ID:	NPC202118
*Common Name:**	1Isopimara-8(14),15-Dien-3-One
IUPAC Name:	(4aR,4bS,7R,10aR)-7-ethenyl-1,1,4a,7-tetramethyl-3,4,4b,5,6,9,10,10a-octahydrophenanthren-2-one
Synonyms:
Standard InCHIKey:	NXPBYMPPPRNGEG-CPLUKWAASA-N
Standard InCHI:	InChI=1S/C20H30O/c1-6-19(4)11-9-15-14(13-19)7-8-16-18(2,3)17(21)10-12-20(15,16)5/h6,13,15-16H,1,7-12H2,2-5H3/t15-,16-,19-,20+/m0/s1
SMILES:	C=C[C@@]1(C)CC[C@H]2C(=C1)CC[C@H]1C(C)(C)C(=O)CC[C@]21C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1099062
PubChem CID:	46887225
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

*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
NPO882	Trogopterus xanthipes	Species	Sciuridae	Eukaryota	feces	n.a.	n.a.	PMID[20402524]
NPO882	Trogopterus xanthipes	Species	Sciuridae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO882	Trogopterus xanthipes	Species	Sciuridae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO882	Trogopterus xanthipes	Species	Sciuridae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO882	Trogopterus xanthipes	Species	Sciuridae	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
IC50	4

Activity Type	# Activity
Cell Line	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT65	Cell Line	HepG2	Homo sapiens	IC50	>	40000.0	nM	PMID[565996]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	40000.0	nM	PMID[565996]
NPT15	Cell Line	Jurkat	Homo sapiens	IC50	>	40000.0	nM	PMID[565996]
NPT466	Cell Line	U-937	Homo sapiens	IC50	>	40000.0	nM	PMID[565996]

☑ 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 NPC202118 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	249
0.1-0.2	2012
0.2-0.3	12439
0.3-0.4	14232
0.4-0.5	7337
0.5-0.6	4409
0.6-0.7	1666
0.7-0.8	284
0.8-0.85	42
0.85-0.9	23
0.9-0.95	1
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC197238
0.9831	High Similarity	NPC469662
0.9194	High Similarity	NPC323005
0.9062	High Similarity	NPC182815
0.9	High Similarity	NPC127582
0.8906	High Similarity	NPC142754
0.8906	High Similarity	NPC296697
0.8906	High Similarity	NPC82477
0.8906	High Similarity	NPC188292
0.8906	High Similarity	NPC39157
0.8906	High Similarity	NPC20610
0.8906	High Similarity	NPC260474
0.8788	High Similarity	NPC470078
0.8788	High Similarity	NPC54123
0.8788	High Similarity	NPC115023
0.8769	High Similarity	NPC139397
0.8769	High Similarity	NPC286814
0.875	High Similarity	NPC20181
0.875	High Similarity	NPC220210
0.8657	High Similarity	NPC251705
0.8636	High Similarity	NPC159577
0.8636	High Similarity	NPC282593
0.8636	High Similarity	NPC251929
0.8636	High Similarity	NPC260040
0.8636	High Similarity	NPC307176
0.8636	High Similarity	NPC35734
0.8636	High Similarity	NPC265782
0.8636	High Similarity	NPC2634
0.8615	High Similarity	NPC310992
0.8615	High Similarity	NPC87141
0.8571	High Similarity	NPC285371
0.8571	High Similarity	NPC475124
0.8548	High Similarity	NPC60565
0.8529	High Similarity	NPC309852
0.8525	High Similarity	NPC472304
0.8525	High Similarity	NPC276764
0.8507	High Similarity	NPC225467
0.8507	High Similarity	NPC190035
0.8507	High Similarity	NPC234707
0.8475	Intermediate Similarity	NPC200258
0.8438	Intermediate Similarity	NPC268039
0.8438	Intermediate Similarity	NPC251118
0.8413	Intermediate Similarity	NPC288253
0.8406	Intermediate Similarity	NPC293803
0.8406	Intermediate Similarity	NPC473171
0.8382	Intermediate Similarity	NPC303613
0.8382	Intermediate Similarity	NPC474488
0.8382	Intermediate Similarity	NPC474228
0.8382	Intermediate Similarity	NPC470045
0.8382	Intermediate Similarity	NPC470044
0.8361	Intermediate Similarity	NPC60772
0.8361	Intermediate Similarity	NPC27610
0.8361	Intermediate Similarity	NPC56905
0.8358	Intermediate Similarity	NPC477856
0.8358	Intermediate Similarity	NPC40574
0.8358	Intermediate Similarity	NPC214770
0.8333	Intermediate Similarity	NPC155198
0.8286	Intermediate Similarity	NPC69408
0.8254	Intermediate Similarity	NPC213152
0.8235	Intermediate Similarity	NPC305501
0.8209	Intermediate Similarity	NPC256846
0.8197	Intermediate Similarity	NPC115385
0.8182	Intermediate Similarity	NPC193770
0.8103	Intermediate Similarity	NPC236623
0.8065	Intermediate Similarity	NPC311852
0.8056	Intermediate Similarity	NPC82635
0.8056	Intermediate Similarity	NPC470052
0.803	Intermediate Similarity	NPC92327
0.8028	Intermediate Similarity	NPC1254
0.8	Intermediate Similarity	NPC103958
0.8	Intermediate Similarity	NPC283908
0.8	Intermediate Similarity	NPC183503
0.8	Intermediate Similarity	NPC474796
0.8	Intermediate Similarity	NPC255021
0.8	Intermediate Similarity	NPC6697
0.8	Intermediate Similarity	NPC251970
0.8	Intermediate Similarity	NPC476046
0.8	Intermediate Similarity	NPC166797
0.8	Intermediate Similarity	NPC474797
0.8	Intermediate Similarity	NPC241854
0.8	Intermediate Similarity	NPC329866
0.8	Intermediate Similarity	NPC212210
0.8	Intermediate Similarity	NPC161923
0.7971	Intermediate Similarity	NPC181204
0.7971	Intermediate Similarity	NPC133253
0.7931	Intermediate Similarity	NPC116906
0.7917	Intermediate Similarity	NPC165711
0.7917	Intermediate Similarity	NPC472300
0.7917	Intermediate Similarity	NPC91665
0.791	Intermediate Similarity	NPC176107
0.7903	Intermediate Similarity	NPC267626
0.7903	Intermediate Similarity	NPC230823
0.7903	Intermediate Similarity	NPC49575
0.7903	Intermediate Similarity	NPC55004
0.7887	Intermediate Similarity	NPC255650
0.7887	Intermediate Similarity	NPC279666
0.7887	Intermediate Similarity	NPC476346
0.7887	Intermediate Similarity	NPC192540
0.7857	Intermediate Similarity	NPC130016
0.7857	Intermediate Similarity	NPC109576
0.7857	Intermediate Similarity	NPC180015
0.7857	Intermediate Similarity	NPC56747
0.7838	Intermediate Similarity	NPC474509
0.7838	Intermediate Similarity	NPC476809
0.7808	Intermediate Similarity	NPC115515
0.7778	Intermediate Similarity	NPC69143
0.7778	Intermediate Similarity	NPC308108
0.7778	Intermediate Similarity	NPC170799
0.7778	Intermediate Similarity	NPC94991
0.7778	Intermediate Similarity	NPC469796
0.7778	Intermediate Similarity	NPC30215
0.7778	Intermediate Similarity	NPC266295
0.7778	Intermediate Similarity	NPC469793
0.7761	Intermediate Similarity	NPC107704
0.7761	Intermediate Similarity	NPC189917
0.7761	Intermediate Similarity	NPC96812
0.7761	Intermediate Similarity	NPC168824
0.7761	Intermediate Similarity	NPC39462
0.7761	Intermediate Similarity	NPC43300
0.7746	Intermediate Similarity	NPC219232
0.7746	Intermediate Similarity	NPC20025
0.7746	Intermediate Similarity	NPC211641
0.7746	Intermediate Similarity	NPC128346
0.7733	Intermediate Similarity	NPC14151
0.7727	Intermediate Similarity	NPC4638
0.7714	Intermediate Similarity	NPC5701
0.7714	Intermediate Similarity	NPC21944
0.7714	Intermediate Similarity	NPC474562
0.7703	Intermediate Similarity	NPC474113
0.7703	Intermediate Similarity	NPC476177
0.7671	Intermediate Similarity	NPC470557
0.7656	Intermediate Similarity	NPC259261
0.7647	Intermediate Similarity	NPC4370
0.7647	Intermediate Similarity	NPC290350
0.7647	Intermediate Similarity	NPC475523
0.7639	Intermediate Similarity	NPC65650
0.7632	Intermediate Similarity	NPC238991
0.7632	Intermediate Similarity	NPC302661
0.7619	Intermediate Similarity	NPC192427
0.76	Intermediate Similarity	NPC2482
0.76	Intermediate Similarity	NPC267517
0.76	Intermediate Similarity	NPC472478
0.7576	Intermediate Similarity	NPC165695
0.7568	Intermediate Similarity	NPC275494
0.7568	Intermediate Similarity	NPC189485
0.7568	Intermediate Similarity	NPC471409
0.7541	Intermediate Similarity	NPC14002
0.7541	Intermediate Similarity	NPC23117
0.7541	Intermediate Similarity	NPC268564
0.7538	Intermediate Similarity	NPC25853
0.7534	Intermediate Similarity	NPC180886
0.75	Intermediate Similarity	NPC471898
0.75	Intermediate Similarity	NPC267691
0.75	Intermediate Similarity	NPC278459
0.75	Intermediate Similarity	NPC3753
0.75	Intermediate Similarity	NPC237591
0.75	Intermediate Similarity	NPC225515
0.75	Intermediate Similarity	NPC27438
0.75	Intermediate Similarity	NPC176171
0.75	Intermediate Similarity	NPC474955
0.75	Intermediate Similarity	NPC64866
0.75	Intermediate Similarity	NPC3915
0.75	Intermediate Similarity	NPC263272
0.75	Intermediate Similarity	NPC274050
0.75	Intermediate Similarity	NPC147066
0.75	Intermediate Similarity	NPC121984
0.75	Intermediate Similarity	NPC475833
0.75	Intermediate Similarity	NPC162632
0.7467	Intermediate Similarity	NPC215843
0.7467	Intermediate Similarity	NPC231431
0.7467	Intermediate Similarity	NPC27817
0.7467	Intermediate Similarity	NPC170793
0.7467	Intermediate Similarity	NPC90965
0.7465	Intermediate Similarity	NPC160817
0.7465	Intermediate Similarity	NPC223187
0.7463	Intermediate Similarity	NPC169275
0.7463	Intermediate Similarity	NPC52449
0.746	Intermediate Similarity	NPC473733
0.7432	Intermediate Similarity	NPC471899
0.7432	Intermediate Similarity	NPC471897
0.7432	Intermediate Similarity	NPC107039
0.7432	Intermediate Similarity	NPC325946
0.7429	Intermediate Similarity	NPC477857
0.7424	Intermediate Similarity	NPC475795
0.7419	Intermediate Similarity	NPC5626
0.7419	Intermediate Similarity	NPC63396
0.7419	Intermediate Similarity	NPC202850
0.7403	Intermediate Similarity	NPC320514
0.7403	Intermediate Similarity	NPC163236
0.7403	Intermediate Similarity	NPC472867
0.7403	Intermediate Similarity	NPC69101
0.7403	Intermediate Similarity	NPC251779
0.7403	Intermediate Similarity	NPC328351
0.7403	Intermediate Similarity	NPC48362
0.7403	Intermediate Similarity	NPC472239
0.7403	Intermediate Similarity	NPC212083
0.7403	Intermediate Similarity	NPC193347
0.7403	Intermediate Similarity	NPC151519
0.7403	Intermediate Similarity	NPC310989
0.7397	Intermediate Similarity	NPC476844

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 NPC202118 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	239
0.1-0.2	2116
0.2-0.3	4386
0.3-0.4	1715
0.4-0.5	372
0.5-0.6	199
0.6-0.7	100
0.7-0.8	18
0.8-0.85	3
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8906	High Similarity	NPD3621	Clinical (unspecified phase)
0.8769	High Similarity	NPD4137	Phase 3
0.8636	High Similarity	NPD4747	Approved
0.8636	High Similarity	NPD4691	Approved
0.8529	High Similarity	NPD4058	Approved
0.8261	Intermediate Similarity	NPD4687	Approved
0.8235	Intermediate Similarity	NPD5276	Approved
0.8	Intermediate Similarity	NPD5733	Approved
0.7778	Intermediate Similarity	NPD287	Approved
0.76	Intermediate Similarity	NPD4695	Discontinued
0.7403	Intermediate Similarity	NPD4223	Phase 3
0.7403	Intermediate Similarity	NPD3667	Approved
0.7403	Intermediate Similarity	NPD4221	Approved
0.7308	Intermediate Similarity	NPD3527	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD8028	Phase 2
0.725	Intermediate Similarity	NPD4623	Approved
0.725	Intermediate Similarity	NPD4519	Discontinued
0.7215	Intermediate Similarity	NPD4786	Approved
0.7215	Intermediate Similarity	NPD3668	Phase 3
0.7215	Intermediate Similarity	NPD4197	Approved
0.7215	Intermediate Similarity	NPD3665	Phase 1
0.7215	Intermediate Similarity	NPD3133	Approved
0.7215	Intermediate Similarity	NPD3666	Approved
0.716	Intermediate Similarity	NPD3573	Approved
0.7125	Intermediate Similarity	NPD5329	Approved
0.7105	Intermediate Similarity	NPD3617	Approved
0.7037	Intermediate Similarity	NPD4693	Phase 3
0.7037	Intermediate Similarity	NPD5690	Phase 2
0.7037	Intermediate Similarity	NPD7521	Approved
0.7037	Intermediate Similarity	NPD7334	Approved
0.7037	Intermediate Similarity	NPD5330	Approved
0.7037	Intermediate Similarity	NPD6098	Approved
0.7037	Intermediate Similarity	NPD4689	Approved
0.7037	Intermediate Similarity	NPD6409	Approved
0.7037	Intermediate Similarity	NPD7146	Approved
0.7037	Intermediate Similarity	NPD6684	Approved
0.7037	Intermediate Similarity	NPD3618	Phase 1
0.7037	Intermediate Similarity	NPD4690	Approved
0.7037	Intermediate Similarity	NPD4688	Approved
0.7037	Intermediate Similarity	NPD5205	Approved
0.7037	Intermediate Similarity	NPD4138	Approved
0.6867	Remote Similarity	NPD5208	Approved
0.6867	Remote Similarity	NPD5737	Approved
0.6867	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD6672	Approved
0.6867	Remote Similarity	NPD6903	Approved
0.6829	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD5280	Approved
0.6829	Remote Similarity	NPD4694	Approved
0.6829	Remote Similarity	NPD5279	Phase 3
0.6824	Remote Similarity	NPD6079	Approved
0.6795	Remote Similarity	NPD4195	Approved
0.6786	Remote Similarity	NPD5328	Approved
0.6786	Remote Similarity	NPD4753	Phase 2
0.6786	Remote Similarity	NPD6673	Approved
0.6786	Remote Similarity	NPD6080	Approved
0.6786	Remote Similarity	NPD6904	Approved
0.6706	Remote Similarity	NPD5207	Approved
0.6628	Remote Similarity	NPD5281	Approved
0.6628	Remote Similarity	NPD5284	Approved
0.6628	Remote Similarity	NPD5694	Approved
0.6628	Remote Similarity	NPD7515	Phase 2
0.6628	Remote Similarity	NPD5693	Phase 1
0.6625	Remote Similarity	NPD4692	Approved
0.6625	Remote Similarity	NPD4139	Approved
0.6591	Remote Similarity	NPD4629	Approved
0.6591	Remote Similarity	NPD5210	Approved
0.6588	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD4784	Approved
0.6579	Remote Similarity	NPD4785	Approved
0.6552	Remote Similarity	NPD6399	Phase 3
0.6552	Remote Similarity	NPD4202	Approved
0.6543	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6533	Remote Similarity	NPD4243	Approved
0.6528	Remote Similarity	NPD7331	Phase 2
0.6517	Remote Similarity	NPD5221	Approved
0.6517	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD5222	Approved
0.6512	Remote Similarity	NPD5692	Phase 3
0.6512	Remote Similarity	NPD4096	Approved
0.6477	Remote Similarity	NPD7900	Approved
0.6477	Remote Similarity	NPD6001	Approved
0.6477	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD7748	Approved
0.6471	Remote Similarity	NPD4518	Approved
0.6444	Remote Similarity	NPD5173	Approved
0.6444	Remote Similarity	NPD3495	Discontinued
0.6441	Remote Similarity	NPD1799	Clinical (unspecified phase)
0.6437	Remote Similarity	NPD6050	Approved
0.6404	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6349	Remote Similarity	NPD8262	Approved
0.6333	Remote Similarity	NPD4697	Phase 3
0.6304	Remote Similarity	NPD5285	Approved
0.6304	Remote Similarity	NPD5286	Approved
0.6304	Remote Similarity	NPD4696	Approved
0.6296	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6282	Remote Similarity	NPD7339	Approved
0.6282	Remote Similarity	NPD8039	Approved
0.6282	Remote Similarity	NPD5275	Approved
0.6282	Remote Similarity	NPD6942	Approved
0.6282	Remote Similarity	NPD4190	Phase 3
0.6265	Remote Similarity	NPD4788	Approved
0.6264	Remote Similarity	NPD4755	Approved
0.6264	Remote Similarity	NPD6083	Phase 2
0.6264	Remote Similarity	NPD6084	Phase 2
0.6264	Remote Similarity	NPD7902	Approved
0.6237	Remote Similarity	NPD5223	Approved
0.6222	Remote Similarity	NPD5695	Phase 3
0.6203	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6197	Remote Similarity	NPD4194	Approved
0.6197	Remote Similarity	NPD4193	Approved
0.6197	Remote Similarity	NPD4192	Approved
0.6197	Remote Similarity	NPD4191	Approved
0.6196	Remote Similarity	NPD5696	Approved
0.6184	Remote Similarity	NPD7144	Approved
0.6184	Remote Similarity	NPD7143	Approved
0.618	Remote Similarity	NPD5133	Approved
0.6176	Remote Similarity	NPD4219	Approved
0.617	Remote Similarity	NPD5211	Phase 2
0.617	Remote Similarity	NPD5225	Approved
0.617	Remote Similarity	NPD4633	Approved
0.617	Remote Similarity	NPD5224	Approved
0.617	Remote Similarity	NPD5226	Approved
0.617	Remote Similarity	NPD5091	Approved
0.6164	Remote Similarity	NPD7341	Phase 2
0.6154	Remote Similarity	NPD7614	Phase 1
0.6154	Remote Similarity	NPD7732	Phase 3
0.6129	Remote Similarity	NPD4700	Approved
0.6118	Remote Similarity	NPD1694	Approved
0.6111	Remote Similarity	NPD5769	Clinical (unspecified phase)
0.6105	Remote Similarity	NPD5175	Approved
0.6105	Remote Similarity	NPD5174	Approved
0.6104	Remote Similarity	NPD7150	Approved
0.6104	Remote Similarity	NPD7151	Approved
0.6104	Remote Similarity	NPD7152	Approved
0.6067	Remote Similarity	NPD6411	Approved
0.6053	Remote Similarity	NPD6922	Approved
0.6053	Remote Similarity	NPD6923	Approved
0.6049	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6044	Remote Similarity	NPD5654	Approved
0.6042	Remote Similarity	NPD5141	Approved
0.6027	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6	Remote Similarity	NPD7631	Approved
0.5976	Remote Similarity	NPD7645	Phase 2
0.5974	Remote Similarity	NPD6938	Clinical (unspecified phase)
0.5974	Remote Similarity	NPD6939	Phase 2
0.5938	Remote Similarity	NPD6052	Approved
0.5938	Remote Similarity	NPD4754	Approved
0.5932	Remote Similarity	NPD5783	Phase 3
0.593	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5918	Remote Similarity	NPD5697	Approved
0.5918	Remote Similarity	NPD6614	Approved
0.5914	Remote Similarity	NPD5959	Approved
0.5889	Remote Similarity	NPD7609	Phase 3
0.5875	Remote Similarity	NPD8264	Approved
0.5867	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.5867	Remote Similarity	NPD4224	Phase 2
0.5859	Remote Similarity	NPD4729	Approved
0.5859	Remote Similarity	NPD5168	Approved
0.5859	Remote Similarity	NPD6881	Approved
0.5859	Remote Similarity	NPD4730	Approved
0.5859	Remote Similarity	NPD6011	Approved
0.5859	Remote Similarity	NPD6899	Approved
0.5843	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5843	Remote Similarity	NPD6101	Approved
0.5816	Remote Similarity	NPD6675	Approved
0.5816	Remote Similarity	NPD6008	Approved
0.5816	Remote Similarity	NPD7128	Approved
0.5816	Remote Similarity	NPD4767	Approved
0.5816	Remote Similarity	NPD5739	Approved
0.5816	Remote Similarity	NPD4768	Approved
0.5816	Remote Similarity	NPD6402	Approved
0.58	Remote Similarity	NPD6012	Approved
0.58	Remote Similarity	NPD6014	Approved
0.58	Remote Similarity	NPD6013	Approved
0.5797	Remote Similarity	NPD4627	Clinical (unspecified phase)
0.5758	Remote Similarity	NPD6412	Phase 2
0.5758	Remote Similarity	NPD5701	Approved
0.575	Remote Similarity	NPD6924	Approved
0.575	Remote Similarity	NPD6926	Approved
0.5743	Remote Similarity	NPD7290	Approved
0.5743	Remote Similarity	NPD5169	Approved
0.5743	Remote Similarity	NPD4634	Approved
0.5743	Remote Similarity	NPD7102	Approved
0.5743	Remote Similarity	NPD5250	Approved
0.5743	Remote Similarity	NPD5247	Approved
0.5743	Remote Similarity	NPD5251	Approved
0.5743	Remote Similarity	NPD5135	Approved
0.5743	Remote Similarity	NPD5248	Approved
0.5743	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.5743	Remote Similarity	NPD5249	Phase 3
0.5743	Remote Similarity	NPD6883	Approved
0.5733	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.5732	Remote Similarity	NPD6932	Approved
0.5714	Remote Similarity	NPD5360	Phase 3
0.5714	Remote Similarity	NPD7812	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD7525	Registered
0.5714	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.57	Remote Similarity	NPD5128	Approved
0.57	Remote Similarity	NPD7320	Approved

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