NPASS Compound

Structure

CID166797 OpenBabel06191715542D 23 25 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 -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 0.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0000 1.7321 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 0.8660 -1.5000 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 0.0000 -2.0000 0.0000 C 0 0 0 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 -2.5981 -3.5000 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 2 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 -0.5000 0.8660 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 2 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 -0.0000 1.7321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 2 0 0 0 0 5 23 1 0 0 0 0 6 19 1 0 0 0 0 7 11 1 0 0 0 0 7 12 1 0 0 0 0 8 9 1 0 0 0 0 8 15 1 0 0 0 0 9 17 1 0 0 0 0 10 13 1 0 0 0 0 10 16 1 0 0 0 0 11 20 1 0 0 0 0 12 21 1 0 0 0 0 13 19 1 0 0 0 0 14 15 2 0 0 0 0 14 19 1 0 0 0 0 15 16 1 0 0 0 0 16 20 1 6 0 0 0 17 20 1 6 0 0 0 17 21 1 0 0 0 0 18 21 1 0 0 0 0 18 22 2 0 0 0 0 18 23 1 0 0 0 0 19 2 1 1 0 0 0 20 3 1 6 0 0 0 21 4 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	316.24
Volume:	355.774
LogP:	4.941
LogD:	3.905
LogS:	-5.139
# Rotatable Bonds:	3
TPSA:	26.3
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.511
Synthetic Accessibility Score:	4.371
Fsp3:	0.762
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:	-4.749
MDCK Permeability:	1.5691928638261743e-05
Pgp-inhibitor:	0.99
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.285
30% Bioavailability (F30%):	0.069

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.098
Plasma Protein Binding (PPB):	95.48493957519531%
Volume Distribution (VD):	0.995
Pgp-substrate:	3.718322515487671%

ADMET: Metabolism

CYP1A2-inhibitor:	0.232
CYP1A2-substrate:	0.612
CYP2C19-inhibitor:	0.222
CYP2C19-substrate:	0.826
CYP2C9-inhibitor:	0.27
CYP2C9-substrate:	0.18
CYP2D6-inhibitor:	0.439
CYP2D6-substrate:	0.182
CYP3A4-inhibitor:	0.957
CYP3A4-substrate:	0.647

ADMET: Excretion

Clearance (CL):	3.36
Half-life (T1/2):	0.156

ADMET: Toxicity

hERG Blockers:	0.044
Human Hepatotoxicity (H-HT):	0.316
Drug-inuced Liver Injury (DILI):	0.374
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.113
Maximum Recommended Daily Dose:	0.545
Skin Sensitization:	0.541
Carcinogencity:	0.779
Eye Corrosion:	0.402
Eye Irritation:	0.449
Respiratory Toxicity:	0.961

Download Data

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

Natural Product: NPC166797

Natural Product ID:	NPC166797
*Common Name:**	Methyl (1R,4As,4Br,7R,10As)-7-Ethenyl-1,4A,7-Trimethyl-3,4,4B,5,6,9,10,10A-Octahydro-2H-Phenanthrene-1-Carboxylate
IUPAC Name:	methyl (1R,4aS,4bR,7R,10aS)-7-ethenyl-1,4a,7-trimethyl-3,4,4b,5,6,9,10,10a-octahydro-2H-phenanthrene-1-carboxylate
Synonyms:
Standard InCHIKey:	BGCXKCIPDDNDEV-GZSKETOLSA-N
Standard InCHI:	InChI=1S/C21H32O2/c1-6-19(2)13-10-16-15(14-19)8-9-17-20(16,3)11-7-12-21(17,4)18(22)23-5/h6,14,16-17H,1,7-13H2,2-5H3/t16-,17+,19+,20+,21-/m1/s1
SMILES:	C=C[C@@]1(C)CC[C@@H]2C(=C1)CC[C@H]1[C@@]2(C)CCC[C@@]1(C)C(=O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2420229
PubChem CID:	73350768
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
NPO26779	Helianthus strumosus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26779	Helianthus strumosus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12676	Berberis mingetsensis	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26558	Physocarpus capitatus	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26852	Cryptocarya konishii	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26114	Dorstenia convexa	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9277	Ammothamnus songoricus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10843	Melanelixia subglabra	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4202	Kopsia terengganensis	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26779	Helianthus strumosus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26706	Dictyota pardalis	Species	Dictyotaceae	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
Others	1

Activity Type	# Activity
Tissue	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT177	Tissue	Aorta	Rattus norvegicus	Inhibition	=	10.5	%	PMID[544289]

☑ 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 NPC166797 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	194
0.1-0.2	1208
0.2-0.3	5875
0.3-0.4	16628
0.4-0.5	7790
0.5-0.6	6192
0.6-0.7	3611
0.7-0.8	1088
0.8-0.85	85
0.85-0.9	12
0.9-0.95	13
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9167	High Similarity	NPC899
0.9155	High Similarity	NPC103958
0.9155	High Similarity	NPC283908
0.9155	High Similarity	NPC161923
0.9155	High Similarity	NPC183503
0.9041	High Similarity	NPC472300
0.9028	High Similarity	NPC192540
0.9028	High Similarity	NPC279666
0.8933	High Similarity	NPC104545
0.8933	High Similarity	NPC267517
0.8919	High Similarity	NPC4827
0.8904	High Similarity	NPC69143
0.8889	High Similarity	NPC241854
0.8889	High Similarity	NPC251970
0.8889	High Similarity	NPC306928
0.8889	High Similarity	NPC476046
0.8816	High Similarity	NPC474955
0.8784	High Similarity	NPC471899
0.8784	High Similarity	NPC107039
0.8784	High Similarity	NPC471897
0.8767	High Similarity	NPC476844
0.8684	High Similarity	NPC477057
0.8667	High Similarity	NPC260385
0.8667	High Similarity	NPC321514
0.8667	High Similarity	NPC110094
0.8667	High Similarity	NPC280654
0.8649	High Similarity	NPC89294
0.863	High Similarity	NPC237591
0.863	High Similarity	NPC3753
0.8611	High Similarity	NPC160817
0.859	High Similarity	NPC200752
0.8553	High Similarity	NPC327674
0.8553	High Similarity	NPC16394
0.8553	High Similarity	NPC199595
0.8553	High Similarity	NPC231431
0.8533	High Similarity	NPC165711
0.85	High Similarity	NPC264127
0.8493	Intermediate Similarity	NPC279241
0.8481	Intermediate Similarity	NPC312660
0.8462	Intermediate Similarity	NPC100297
0.8442	Intermediate Similarity	NPC37038
0.8421	Intermediate Similarity	NPC179028
0.8421	Intermediate Similarity	NPC239098
0.84	Intermediate Similarity	NPC309399
0.84	Intermediate Similarity	NPC41017
0.8375	Intermediate Similarity	NPC76333
0.8375	Intermediate Similarity	NPC470223
0.8375	Intermediate Similarity	NPC2709
0.8333	Intermediate Similarity	NPC142244
0.8333	Intermediate Similarity	NPC274050
0.8333	Intermediate Similarity	NPC162632
0.8333	Intermediate Similarity	NPC229584
0.8333	Intermediate Similarity	NPC267691
0.8333	Intermediate Similarity	NPC147066
0.8333	Intermediate Similarity	NPC278459
0.8333	Intermediate Similarity	NPC40228
0.8333	Intermediate Similarity	NPC221647
0.8333	Intermediate Similarity	NPC14203
0.8333	Intermediate Similarity	NPC263272
0.8333	Intermediate Similarity	NPC471898
0.8333	Intermediate Similarity	NPC327002
0.8293	Intermediate Similarity	NPC472220
0.8293	Intermediate Similarity	NPC97884
0.8272	Intermediate Similarity	NPC9892
0.8272	Intermediate Similarity	NPC10005
0.8272	Intermediate Similarity	NPC329943
0.8272	Intermediate Similarity	NPC325594
0.8272	Intermediate Similarity	NPC91525
0.8272	Intermediate Similarity	NPC324063
0.8272	Intermediate Similarity	NPC195640
0.8272	Intermediate Similarity	NPC73038
0.8267	Intermediate Similarity	NPC201027
0.825	Intermediate Similarity	NPC156981
0.8228	Intermediate Similarity	NPC238991
0.8228	Intermediate Similarity	NPC142683
0.8228	Intermediate Similarity	NPC251779
0.8228	Intermediate Similarity	NPC240302
0.8228	Intermediate Similarity	NPC69101
0.8228	Intermediate Similarity	NPC302661
0.8219	Intermediate Similarity	NPC91369
0.8194	Intermediate Similarity	NPC290445
0.8194	Intermediate Similarity	NPC36616
0.8182	Intermediate Similarity	NPC35574
0.8182	Intermediate Similarity	NPC59436
0.8171	Intermediate Similarity	NPC162107
0.8171	Intermediate Similarity	NPC46912
0.8148	Intermediate Similarity	NPC29447
0.8148	Intermediate Similarity	NPC474537
0.8148	Intermediate Similarity	NPC323765
0.8133	Intermediate Similarity	NPC18819
0.8133	Intermediate Similarity	NPC46610
0.8133	Intermediate Similarity	NPC301065
0.8133	Intermediate Similarity	NPC255168
0.8125	Intermediate Similarity	NPC70834
0.8125	Intermediate Similarity	NPC167103
0.8108	Intermediate Similarity	NPC72343
0.8101	Intermediate Similarity	NPC476101
0.8101	Intermediate Similarity	NPC201912
0.8101	Intermediate Similarity	NPC476988
0.8101	Intermediate Similarity	NPC38350
0.8077	Intermediate Similarity	NPC28319
0.8077	Intermediate Similarity	NPC477371
0.8077	Intermediate Similarity	NPC476177
0.8077	Intermediate Similarity	NPC158846
0.8077	Intermediate Similarity	NPC100906
0.8072	Intermediate Similarity	NPC40552
0.8072	Intermediate Similarity	NPC28227
0.8072	Intermediate Similarity	NPC224145
0.8072	Intermediate Similarity	NPC246708
0.8072	Intermediate Similarity	NPC474845
0.8052	Intermediate Similarity	NPC61952
0.8049	Intermediate Similarity	NPC82979
0.8049	Intermediate Similarity	NPC155011
0.8049	Intermediate Similarity	NPC322159
0.8026	Intermediate Similarity	NPC476795
0.8025	Intermediate Similarity	NPC100391
0.8025	Intermediate Similarity	NPC96095
0.8025	Intermediate Similarity	NPC477289
0.8025	Intermediate Similarity	NPC139566
0.8	Intermediate Similarity	NPC218301
0.8	Intermediate Similarity	NPC202118
0.8	Intermediate Similarity	NPC197238
0.8	Intermediate Similarity	NPC260956
0.8	Intermediate Similarity	NPC200513
0.8	Intermediate Similarity	NPC321289
0.8	Intermediate Similarity	NPC163236
0.8	Intermediate Similarity	NPC470237
0.8	Intermediate Similarity	NPC36310
0.8	Intermediate Similarity	NPC327969
0.8	Intermediate Similarity	NPC73882
0.8	Intermediate Similarity	NPC320514
0.7976	Intermediate Similarity	NPC469546
0.7976	Intermediate Similarity	NPC475049
0.7976	Intermediate Similarity	NPC470588
0.7976	Intermediate Similarity	NPC474700
0.7976	Intermediate Similarity	NPC474570
0.7975	Intermediate Similarity	NPC195424
0.7975	Intermediate Similarity	NPC474956
0.7975	Intermediate Similarity	NPC2482
0.7952	Intermediate Similarity	NPC102683
0.7952	Intermediate Similarity	NPC51700
0.7952	Intermediate Similarity	NPC171203
0.7952	Intermediate Similarity	NPC130577
0.7952	Intermediate Similarity	NPC71507
0.7952	Intermediate Similarity	NPC18064
0.7952	Intermediate Similarity	NPC128644
0.7952	Intermediate Similarity	NPC88716
0.7952	Intermediate Similarity	NPC98442
0.7952	Intermediate Similarity	NPC242468
0.7952	Intermediate Similarity	NPC307426
0.7952	Intermediate Similarity	NPC477926
0.7952	Intermediate Similarity	NPC30421
0.7952	Intermediate Similarity	NPC293564
0.7952	Intermediate Similarity	NPC68160
0.7952	Intermediate Similarity	NPC142415
0.7952	Intermediate Similarity	NPC96496
0.7952	Intermediate Similarity	NPC474684
0.7952	Intermediate Similarity	NPC477228
0.7952	Intermediate Similarity	NPC158141
0.7952	Intermediate Similarity	NPC173089
0.7952	Intermediate Similarity	NPC142361
0.7949	Intermediate Similarity	NPC198240
0.7949	Intermediate Similarity	NPC63020
0.7927	Intermediate Similarity	NPC283733
0.7927	Intermediate Similarity	NPC474680
0.7922	Intermediate Similarity	NPC476601
0.7922	Intermediate Similarity	NPC180886
0.7922	Intermediate Similarity	NPC40353
0.7901	Intermediate Similarity	NPC477852
0.7901	Intermediate Similarity	NPC102197
0.7901	Intermediate Similarity	NPC215893
0.7901	Intermediate Similarity	NPC69279
0.7901	Intermediate Similarity	NPC83569
0.7901	Intermediate Similarity	NPC470046
0.7901	Intermediate Similarity	NPC470047
0.7901	Intermediate Similarity	NPC312480
0.7887	Intermediate Similarity	NPC469662
0.7882	Intermediate Similarity	NPC198818
0.7882	Intermediate Similarity	NPC474728
0.7882	Intermediate Similarity	NPC120840
0.7882	Intermediate Similarity	NPC113989
0.7882	Intermediate Similarity	NPC471896
0.7882	Intermediate Similarity	NPC476369
0.7882	Intermediate Similarity	NPC159748
0.7882	Intermediate Similarity	NPC328141
0.7882	Intermediate Similarity	NPC476437
0.7882	Intermediate Similarity	NPC101651
0.7875	Intermediate Similarity	NPC3915
0.7875	Intermediate Similarity	NPC142163
0.7875	Intermediate Similarity	NPC14151
0.7875	Intermediate Similarity	NPC473420
0.7875	Intermediate Similarity	NPC477372
0.7875	Intermediate Similarity	NPC90055
0.7875	Intermediate Similarity	NPC475665
0.7857	Intermediate Similarity	NPC17733
0.7857	Intermediate Similarity	NPC24816
0.7857	Intermediate Similarity	NPC470629
0.7857	Intermediate Similarity	NPC1753
0.7857	Intermediate Similarity	NPC182797
0.7857	Intermediate Similarity	NPC474512

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 NPC166797 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	179
0.1-0.2	1469
0.2-0.3	4118
0.3-0.4	2273
0.4-0.5	640
0.5-0.6	256
0.6-0.7	155
0.7-0.8	53
0.8-0.85	7
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8272	Intermediate Similarity	NPD7521	Approved
0.8272	Intermediate Similarity	NPD6684	Approved
0.8272	Intermediate Similarity	NPD6409	Approved
0.8272	Intermediate Similarity	NPD5330	Approved
0.8272	Intermediate Similarity	NPD7146	Approved
0.8272	Intermediate Similarity	NPD7334	Approved
0.8072	Intermediate Similarity	NPD6672	Approved
0.8072	Intermediate Similarity	NPD5737	Approved
0.8072	Intermediate Similarity	NPD6903	Approved
0.8072	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.8049	Intermediate Similarity	NPD6098	Approved
0.8	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7952	Intermediate Similarity	NPD3573	Approved
0.7792	Intermediate Similarity	NPD8039	Approved
0.7765	Intermediate Similarity	NPD6673	Approved
0.7765	Intermediate Similarity	NPD6080	Approved
0.7765	Intermediate Similarity	NPD6904	Approved
0.7701	Intermediate Similarity	NPD6399	Phase 3
0.7647	Intermediate Similarity	NPD5208	Approved
0.7614	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7614	Intermediate Similarity	NPD7748	Approved
0.7614	Intermediate Similarity	NPD7900	Approved
0.759	Intermediate Similarity	NPD4786	Approved
0.7586	Intermediate Similarity	NPD7515	Phase 2
0.7561	Intermediate Similarity	NPD3667	Approved
0.7531	Intermediate Similarity	NPD4695	Discontinued
0.7528	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD5207	Approved
0.7386	Intermediate Similarity	NPD5693	Phase 1
0.7386	Intermediate Similarity	NPD5694	Approved
0.7386	Intermediate Similarity	NPD6050	Approved
0.7386	Intermediate Similarity	NPD6411	Approved
0.7381	Intermediate Similarity	NPD3668	Phase 3
0.7381	Intermediate Similarity	NPD3133	Approved
0.7381	Intermediate Similarity	NPD3666	Approved
0.7381	Intermediate Similarity	NPD3665	Phase 1
0.7368	Intermediate Similarity	NPD4137	Phase 3
0.7363	Intermediate Similarity	NPD6084	Phase 2
0.7363	Intermediate Similarity	NPD6083	Phase 2
0.7363	Intermediate Similarity	NPD7902	Approved
0.7356	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD4223	Phase 3
0.7349	Intermediate Similarity	NPD4221	Approved
0.7294	Intermediate Similarity	NPD5329	Approved
0.7273	Intermediate Similarity	NPD4691	Approved
0.7273	Intermediate Similarity	NPD5692	Phase 3
0.7273	Intermediate Similarity	NPD4747	Approved
0.7253	Intermediate Similarity	NPD7732	Phase 3
0.7237	Intermediate Similarity	NPD3621	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD6001	Approved
0.7215	Intermediate Similarity	NPD4058	Approved
0.7209	Intermediate Similarity	NPD3618	Phase 1
0.7209	Intermediate Similarity	NPD4623	Approved
0.7209	Intermediate Similarity	NPD4519	Discontinued
0.7191	Intermediate Similarity	NPD5281	Approved
0.7191	Intermediate Similarity	NPD6079	Approved
0.7191	Intermediate Similarity	NPD5284	Approved
0.7176	Intermediate Similarity	NPD4197	Approved
0.7159	Intermediate Similarity	NPD6101	Approved
0.7159	Intermediate Similarity	NPD5328	Approved
0.7159	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5695	Phase 3
0.7097	Intermediate Similarity	NPD5696	Approved
0.7093	Intermediate Similarity	NPD1694	Approved
0.7093	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD3617	Approved
0.7011	Intermediate Similarity	NPD4693	Phase 3
0.7011	Intermediate Similarity	NPD5279	Phase 3
0.7011	Intermediate Similarity	NPD4689	Approved
0.7011	Intermediate Similarity	NPD4138	Approved
0.7011	Intermediate Similarity	NPD4690	Approved
0.7011	Intermediate Similarity	NPD5205	Approved
0.7011	Intermediate Similarity	NPD5690	Phase 2
0.7011	Intermediate Similarity	NPD4688	Approved
0.7	Intermediate Similarity	NPD4687	Approved
0.7	Intermediate Similarity	NPD5733	Approved
0.6966	Remote Similarity	NPD4753	Phase 2
0.6966	Remote Similarity	NPD6051	Approved
0.6962	Remote Similarity	NPD5276	Approved
0.6912	Remote Similarity	NPD28	Approved
0.6912	Remote Similarity	NPD29	Approved
0.6882	Remote Similarity	NPD7614	Phase 1
0.6882	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD6899	Approved
0.6869	Remote Similarity	NPD6881	Approved
0.6837	Remote Similarity	NPD5739	Approved
0.6837	Remote Similarity	NPD6675	Approved
0.6837	Remote Similarity	NPD6402	Approved
0.6837	Remote Similarity	NPD7128	Approved
0.6818	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD4694	Approved
0.6818	Remote Similarity	NPD5280	Approved
0.6813	Remote Similarity	NPD8034	Phase 2
0.6813	Remote Similarity	NPD8035	Phase 2
0.6804	Remote Similarity	NPD6052	Approved
0.679	Remote Similarity	NPD4784	Approved
0.679	Remote Similarity	NPD4785	Approved
0.6786	Remote Similarity	NPD4195	Approved
0.6786	Remote Similarity	NPD7645	Phase 2
0.6774	Remote Similarity	NPD4629	Approved
0.6774	Remote Similarity	NPD5654	Approved
0.6774	Remote Similarity	NPD5210	Approved
0.6768	Remote Similarity	NPD6614	Approved
0.6768	Remote Similarity	NPD5697	Approved
0.675	Remote Similarity	NPD5777	Approved
0.675	Remote Similarity	NPD4243	Approved
0.6739	Remote Similarity	NPD5778	Approved
0.6739	Remote Similarity	NPD5779	Approved
0.6739	Remote Similarity	NPD4202	Approved
0.6737	Remote Similarity	NPD7638	Approved
0.6733	Remote Similarity	NPD7102	Approved
0.6733	Remote Similarity	NPD6883	Approved
0.6733	Remote Similarity	NPD7290	Approved
0.6711	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD7339	Approved
0.6707	Remote Similarity	NPD6942	Approved
0.6702	Remote Similarity	NPD5221	Approved
0.6702	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD5222	Approved
0.67	Remote Similarity	NPD6011	Approved
0.67	Remote Similarity	NPD7320	Approved
0.6667	Remote Similarity	NPD7639	Approved
0.6667	Remote Similarity	NPD6404	Discontinued
0.6667	Remote Similarity	NPD4788	Approved
0.6667	Remote Similarity	NPD6869	Approved
0.6667	Remote Similarity	NPD6008	Approved
0.6667	Remote Similarity	NPD6649	Approved
0.6667	Remote Similarity	NPD6847	Approved
0.6667	Remote Similarity	NPD7640	Approved
0.6667	Remote Similarity	NPD8130	Phase 1
0.6667	Remote Similarity	NPD6650	Approved
0.6667	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6617	Approved
0.6634	Remote Similarity	NPD6013	Approved
0.6634	Remote Similarity	NPD6014	Approved
0.6634	Remote Similarity	NPD6012	Approved
0.6634	Remote Similarity	NPD6373	Approved
0.6634	Remote Similarity	NPD6372	Approved
0.6632	Remote Similarity	NPD5173	Approved
0.6632	Remote Similarity	NPD5959	Approved
0.6628	Remote Similarity	NPD4139	Approved
0.6628	Remote Similarity	NPD4692	Approved
0.6627	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.662	Remote Similarity	NPD3196	Approved
0.662	Remote Similarity	NPD4266	Approved
0.662	Remote Similarity	NPD3194	Approved
0.662	Remote Similarity	NPD3195	Phase 2
0.6602	Remote Similarity	NPD6882	Approved
0.6602	Remote Similarity	NPD8297	Approved
0.66	Remote Similarity	NPD5701	Approved
0.6538	Remote Similarity	NPD4224	Phase 2
0.6538	Remote Similarity	NPD7094	Approved
0.6538	Remote Similarity	NPD6858	Approved
0.6538	Remote Similarity	NPD7331	Phase 2
0.6535	Remote Similarity	NPD6686	Approved
0.6526	Remote Similarity	NPD4697	Phase 3
0.6522	Remote Similarity	NPD4096	Approved
0.6505	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6495	Remote Similarity	NPD4696	Approved
0.6495	Remote Similarity	NPD5285	Approved
0.6495	Remote Similarity	NPD5286	Approved
0.6484	Remote Similarity	NPD4518	Approved
0.6479	Remote Similarity	NPD3172	Approved
0.6477	Remote Similarity	NPD5362	Discontinued
0.6458	Remote Similarity	NPD4755	Approved
0.6452	Remote Similarity	NPD7637	Suspended
0.6437	Remote Similarity	NPD5369	Approved
0.6437	Remote Similarity	NPD8028	Phase 2
0.6436	Remote Similarity	NPD6412	Phase 2
0.6429	Remote Similarity	NPD5223	Approved
0.6415	Remote Similarity	NPD6868	Approved
0.641	Remote Similarity	NPD7341	Phase 2
0.6386	Remote Similarity	NPD6926	Approved
0.6386	Remote Similarity	NPD6924	Approved
0.6386	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6381	Remote Similarity	NPD4632	Approved
0.6364	Remote Similarity	NPD5224	Approved
0.6364	Remote Similarity	NPD4633	Approved
0.6364	Remote Similarity	NPD5211	Phase 2
0.6364	Remote Similarity	NPD5225	Approved
0.6364	Remote Similarity	NPD5226	Approved
0.6364	Remote Similarity	NPD6435	Approved
0.6355	Remote Similarity	NPD7115	Discovery
0.6341	Remote Similarity	NPD6081	Approved
0.6329	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD4700	Approved
0.6322	Remote Similarity	NPD7525	Registered
0.6322	Remote Similarity	NPD5368	Approved
0.6316	Remote Similarity	NPD5707	Approved
0.631	Remote Similarity	NPD3702	Approved
0.631	Remote Similarity	NPD5275	Approved
0.631	Remote Similarity	NPD4190	Phase 3
0.63	Remote Similarity	NPD5174	Approved
0.63	Remote Similarity	NPD5175	Approved
0.6296	Remote Similarity	NPD6335	Approved
0.6292	Remote Similarity	NPD7154	Phase 3
0.6292	Remote Similarity	NPD3527	Clinical (unspecified phase)
0.6267	Remote Similarity	NPD287	Approved
0.6264	Remote Similarity	NPD6422	Discontinued
0.625	Remote Similarity	NPD857	Phase 3

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