NPASS Compound

Structure

NPC476314 OpenBabel07101718282D 22 25 0 0 1 0 0 0 0 0999 V2000 7.0032 -0.5341 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5032 0.3320 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8036 1.9574 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4051 -1.0341 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1371 -2.0341 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5391 -0.5341 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0032 -1.5341 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2711 -1.5341 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6730 -0.0341 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1371 0.9659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5391 1.4659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2588 0.9659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4051 0.9659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4051 -0.0341 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2711 1.4659 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.1371 -0.0341 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7071 0.7071 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 6.0032 -0.5341 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6730 0.9659 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.2711 -0.5341 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2711 2.4659 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 1 0 0 0 0 2 18 1 0 0 0 0 5 7 1 0 0 0 0 5 8 1 0 0 0 0 6 9 1 0 0 0 0 6 14 1 0 0 0 0 7 18 1 0 0 0 0 8 20 1 0 0 0 0 9 19 1 0 0 0 0 10 15 1 0 0 0 0 10 16 1 0 0 0 0 11 13 2 0 0 0 0 11 19 1 0 0 0 0 12 17 1 0 0 0 0 12 22 1 0 0 0 0 13 14 1 0 0 0 0 13 15 1 0 0 0 0 14 20 1 1 0 0 0 15 21 1 6 0 0 0 16 18 1 0 0 0 0 16 20 1 1 0 0 0 17 19 1 0 0 0 0 17 22 1 0 0 0 0 19 3 1 1 0 0 0 20 4 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	304.24
Volume:	335.194
LogP:	4.672
LogD:	3.829
LogS:	-5.193
# Rotatable Bonds:	1
TPSA:	32.76
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.578
Synthetic Accessibility Score:	4.608
Fsp3:	0.9
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.61
MDCK Permeability:	2.2997190171736293e-05
Pgp-inhibitor:	0.713
Pgp-substrate:	0.095
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.908
30% Bioavailability (F30%):	0.363

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.109
Plasma Protein Binding (PPB):	91.0599594116211%
Volume Distribution (VD):	1.899
Pgp-substrate:	8.628008842468262%

ADMET: Metabolism

CYP1A2-inhibitor:	0.044
CYP1A2-substrate:	0.354
CYP2C19-inhibitor:	0.054
CYP2C19-substrate:	0.859
CYP2C9-inhibitor:	0.232
CYP2C9-substrate:	0.061
CYP2D6-inhibitor:	0.017
CYP2D6-substrate:	0.259
CYP3A4-inhibitor:	0.851
CYP3A4-substrate:	0.313

ADMET: Excretion

Clearance (CL):	9.413
Half-life (T1/2):	0.071

ADMET: Toxicity

hERG Blockers:	0.055
Human Hepatotoxicity (H-HT):	0.184
Drug-inuced Liver Injury (DILI):	0.047
AMES Toxicity:	0.021
Rat Oral Acute Toxicity:	0.517
Maximum Recommended Daily Dose:	0.939
Skin Sensitization:	0.162
Carcinogencity:	0.257
Eye Corrosion:	0.929
Eye Irritation:	0.902
Respiratory Toxicity:	0.963

Download Data

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

Natural Product: NPC476314

Natural Product ID:	NPC476314
*Common Name:**	Rel-15(Zeta),16-Epoxy-7Alpha-Hydroxypimar-8,14-Ene
IUPAC Name:	(4aS,4bR,7S,9R,10aS)-1,1,4a,7-tetramethyl-7-(oxiran-2-yl)-3,4,4b,5,6,9,10,10a-octahydro-2H-phenanthren-9-ol
Synonyms:
Standard InCHIKey:	MNAWTFGICGSIKM-YKYKTHHOSA-N
Standard InCHI:	InChI=1S/C20H32O2/c1-18(2)7-5-8-20(4)14-6-9-19(3,17-12-22-17)11-13(14)15(21)10-16(18)20/h11,14-17,21H,5-10,12H2,1-4H3/t14-,15+,16-,17?,19-,20+/m0/s1
SMILES:	CC1(CCCC2(C1CC(C3=CC(CCC32)(C)C4CO4)O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL563927
PubChem CID:	44179875
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
NPO25510	Plectranthus ernstii	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19445517]
NPO25510	Plectranthus ernstii	Species	Lamiaceae	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	8

Activity Type	# Activity
Organism	8

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	32.0	ug.mL-1	PMID[543828]
NPT1176	Organism	Mycobacterium fortuitum	Mycobacterium fortuitum	MIC	=	16.0	ug.mL-1	PMID[543828]
NPT1177	Organism	Mycobacterium phlei	Mycobacterium phlei	MIC	=	8.0	ug.mL-1	PMID[543828]
NPT602	Organism	Mycobacterium smegmatis	Mycobacterium smegmatis	MIC	=	16.0	ug.mL-1	PMID[543828]

☑ 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 NPC476314 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	1457
0.2-0.3	5376
0.3-0.4	15472
0.4-0.5	9455
0.5-0.6	6220
0.6-0.7	3540
0.7-0.8	834
0.8-0.85	122
0.85-0.9	26
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9103	High Similarity	NPC475789
0.9067	High Similarity	NPC91594
0.8987	High Similarity	NPC474047
0.8961	High Similarity	NPC96362
0.8947	High Similarity	NPC83351
0.8947	High Similarity	NPC167891
0.8933	High Similarity	NPC253190
0.8919	High Similarity	NPC243342
0.8919	High Similarity	NPC306727
0.8919	High Similarity	NPC477138
0.8904	High Similarity	NPC242001
0.8846	High Similarity	NPC476646
0.8831	High Similarity	NPC109546
0.8831	High Similarity	NPC81306
0.8831	High Similarity	NPC30986
0.8831	High Similarity	NPC84694
0.8831	High Similarity	NPC143182
0.8831	High Similarity	NPC28862
0.8831	High Similarity	NPC209430
0.8831	High Similarity	NPC47982
0.8816	High Similarity	NPC470758
0.8816	High Similarity	NPC470711
0.88	High Similarity	NPC291503
0.88	High Similarity	NPC477923
0.88	High Similarity	NPC66566
0.8784	High Similarity	NPC471799
0.8767	High Similarity	NPC34834
0.8767	High Similarity	NPC145498
0.8718	High Similarity	NPC234193
0.8718	High Similarity	NPC295131
0.8701	High Similarity	NPC474216
0.8684	High Similarity	NPC470749
0.8684	High Similarity	NPC477925
0.8684	High Similarity	NPC274079
0.8684	High Similarity	NPC265588
0.8667	High Similarity	NPC201048
0.8667	High Similarity	NPC476366
0.8667	High Similarity	NPC469534
0.8667	High Similarity	NPC91858
0.8667	High Similarity	NPC469533
0.8667	High Similarity	NPC471797
0.8667	High Similarity	NPC469593
0.8625	High Similarity	NPC317458
0.8611	High Similarity	NPC68703
0.8611	High Similarity	NPC69649
0.8608	High Similarity	NPC474759
0.8608	High Similarity	NPC249423
0.8608	High Similarity	NPC116202
0.8608	High Similarity	NPC264245
0.8608	High Similarity	NPC474683
0.8608	High Similarity	NPC474752
0.8608	High Similarity	NPC7505
0.8608	High Similarity	NPC209620
0.8608	High Similarity	NPC474731
0.8608	High Similarity	NPC82986
0.8608	High Similarity	NPC23852
0.8571	High Similarity	NPC471798
0.8571	High Similarity	NPC477924
0.8533	High Similarity	NPC182717
0.85	High Similarity	NPC50964
0.85	High Similarity	NPC470049
0.85	High Similarity	NPC49964
0.85	High Similarity	NPC304285
0.85	High Similarity	NPC189972
0.85	High Similarity	NPC101462
0.8493	Intermediate Similarity	NPC208999
0.8493	Intermediate Similarity	NPC96484
0.8481	Intermediate Similarity	NPC164840
0.8481	Intermediate Similarity	NPC241290
0.8481	Intermediate Similarity	NPC209944
0.8462	Intermediate Similarity	NPC473943
0.8462	Intermediate Similarity	NPC99168
0.8462	Intermediate Similarity	NPC470396
0.8462	Intermediate Similarity	NPC11908
0.8462	Intermediate Similarity	NPC474989
0.8462	Intermediate Similarity	NPC22955
0.8442	Intermediate Similarity	NPC321016
0.8442	Intermediate Similarity	NPC321381
0.8442	Intermediate Similarity	NPC247325
0.8442	Intermediate Similarity	NPC107059
0.8442	Intermediate Similarity	NPC244488
0.8421	Intermediate Similarity	NPC100334
0.8415	Intermediate Similarity	NPC266511
0.8415	Intermediate Similarity	NPC274448
0.84	Intermediate Similarity	NPC477792
0.84	Intermediate Similarity	NPC167706
0.8395	Intermediate Similarity	NPC474634
0.8378	Intermediate Similarity	NPC9942
0.8375	Intermediate Similarity	NPC142163
0.8375	Intermediate Similarity	NPC159148
0.8375	Intermediate Similarity	NPC47761
0.8356	Intermediate Similarity	NPC114651
0.8354	Intermediate Similarity	NPC53744
0.8354	Intermediate Similarity	NPC291379
0.8354	Intermediate Similarity	NPC100906
0.8333	Intermediate Similarity	NPC157996
0.8333	Intermediate Similarity	NPC34019
0.8333	Intermediate Similarity	NPC40394
0.8333	Intermediate Similarity	NPC155986
0.8333	Intermediate Similarity	NPC34177
0.8333	Intermediate Similarity	NPC472805
0.8333	Intermediate Similarity	NPC198968
0.8333	Intermediate Similarity	NPC90979
0.8333	Intermediate Similarity	NPC101475
0.8333	Intermediate Similarity	NPC318495
0.8313	Intermediate Similarity	NPC261266
0.8313	Intermediate Similarity	NPC6391
0.8312	Intermediate Similarity	NPC288035
0.8312	Intermediate Similarity	NPC171148
0.8312	Intermediate Similarity	NPC230301
0.8312	Intermediate Similarity	NPC304309
0.8312	Intermediate Similarity	NPC69383
0.8312	Intermediate Similarity	NPC162742
0.8312	Intermediate Similarity	NPC136188
0.8312	Intermediate Similarity	NPC257347
0.8312	Intermediate Similarity	NPC285893
0.8312	Intermediate Similarity	NPC313179
0.8312	Intermediate Similarity	NPC22105
0.8312	Intermediate Similarity	NPC134847
0.8312	Intermediate Similarity	NPC141071
0.8312	Intermediate Similarity	NPC32832
0.8312	Intermediate Similarity	NPC471723
0.8312	Intermediate Similarity	NPC28657
0.8293	Intermediate Similarity	NPC238485
0.8293	Intermediate Similarity	NPC470077
0.8293	Intermediate Similarity	NPC185568
0.8293	Intermediate Similarity	NPC205845
0.8289	Intermediate Similarity	NPC68443
0.8289	Intermediate Similarity	NPC220939
0.8289	Intermediate Similarity	NPC265485
0.8272	Intermediate Similarity	NPC87489
0.8272	Intermediate Similarity	NPC155521
0.8272	Intermediate Similarity	NPC296701
0.8272	Intermediate Similarity	NPC218616
0.8272	Intermediate Similarity	NPC202389
0.8267	Intermediate Similarity	NPC92801
0.825	Intermediate Similarity	NPC287749
0.825	Intermediate Similarity	NPC281880
0.8243	Intermediate Similarity	NPC471238
0.8235	Intermediate Similarity	NPC477917
0.8228	Intermediate Similarity	NPC158662
0.8228	Intermediate Similarity	NPC477522
0.8228	Intermediate Similarity	NPC87604
0.8228	Intermediate Similarity	NPC300499
0.8228	Intermediate Similarity	NPC253807
0.8228	Intermediate Similarity	NPC230295
0.8228	Intermediate Similarity	NPC98386
0.8228	Intermediate Similarity	NPC196753
0.8228	Intermediate Similarity	NPC275910
0.8219	Intermediate Similarity	NPC202017
0.8214	Intermediate Similarity	NPC149224
0.8205	Intermediate Similarity	NPC120098
0.8205	Intermediate Similarity	NPC27765
0.8205	Intermediate Similarity	NPC30590
0.8205	Intermediate Similarity	NPC189883
0.8205	Intermediate Similarity	NPC290598
0.8205	Intermediate Similarity	NPC122418
0.8205	Intermediate Similarity	NPC240604
0.8205	Intermediate Similarity	NPC265328
0.8205	Intermediate Similarity	NPC134330
0.8205	Intermediate Similarity	NPC106364
0.8205	Intermediate Similarity	NPC113733
0.8205	Intermediate Similarity	NPC300324
0.8205	Intermediate Similarity	NPC106432
0.8205	Intermediate Similarity	NPC129165
0.8205	Intermediate Similarity	NPC96319
0.8194	Intermediate Similarity	NPC290367
0.8193	Intermediate Similarity	NPC157257
0.8193	Intermediate Similarity	NPC474349
0.8193	Intermediate Similarity	NPC474189
0.8171	Intermediate Similarity	NPC82623
0.8171	Intermediate Similarity	NPC470384
0.8158	Intermediate Similarity	NPC110799
0.8158	Intermediate Similarity	NPC23954
0.8148	Intermediate Similarity	NPC474531
0.814	Intermediate Similarity	NPC295668
0.8133	Intermediate Similarity	NPC474248
0.8133	Intermediate Similarity	NPC471560
0.8125	Intermediate Similarity	NPC1319
0.8125	Intermediate Similarity	NPC472463
0.8125	Intermediate Similarity	NPC328714
0.8118	Intermediate Similarity	NPC474668
0.8118	Intermediate Similarity	NPC67872
0.8118	Intermediate Similarity	NPC471952
0.8108	Intermediate Similarity	NPC197805
0.8101	Intermediate Similarity	NPC214570
0.8101	Intermediate Similarity	NPC130136
0.8095	Intermediate Similarity	NPC293287
0.8095	Intermediate Similarity	NPC152808
0.8095	Intermediate Similarity	NPC125399
0.809	Intermediate Similarity	NPC103165
0.809	Intermediate Similarity	NPC210717
0.8077	Intermediate Similarity	NPC34700
0.8077	Intermediate Similarity	NPC138374
0.8072	Intermediate Similarity	NPC102048
0.8072	Intermediate Similarity	NPC231310
0.8072	Intermediate Similarity	NPC306951
0.8072	Intermediate Similarity	NPC319238
0.8052	Intermediate Similarity	NPC474743
0.8049	Intermediate Similarity	NPC248886

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 NPC476314 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	174
0.1-0.2	1733
0.2-0.3	3999
0.3-0.4	2254
0.4-0.5	603
0.5-0.6	242
0.6-0.7	112
0.7-0.8	33
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
0.8354	Intermediate Similarity	NPD7645	Phase 2
0.8312	Intermediate Similarity	NPD6942	Approved
0.8312	Intermediate Similarity	NPD7339	Approved
0.8312	Intermediate Similarity	NPD8264	Approved
0.8205	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7805	Intermediate Similarity	NPD7525	Registered
0.7791	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD6924	Approved
0.7722	Intermediate Similarity	NPD6926	Approved
0.7683	Intermediate Similarity	NPD6929	Approved
0.7647	Intermediate Similarity	NPD4786	Approved
0.7619	Intermediate Similarity	NPD3667	Approved
0.759	Intermediate Similarity	NPD6930	Phase 2
0.759	Intermediate Similarity	NPD6931	Approved
0.7561	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD6933	Approved
0.7529	Intermediate Similarity	NPD6695	Phase 3
0.75	Intermediate Similarity	NPD6902	Approved
0.7468	Intermediate Similarity	NPD7151	Approved
0.7468	Intermediate Similarity	NPD7150	Approved
0.7468	Intermediate Similarity	NPD7152	Approved
0.7442	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD6925	Approved
0.7439	Intermediate Similarity	NPD5776	Phase 2
0.7436	Intermediate Similarity	NPD6923	Approved
0.7436	Intermediate Similarity	NPD6922	Approved
0.7381	Intermediate Similarity	NPD7332	Phase 2
0.7381	Intermediate Similarity	NPD7514	Phase 3
0.7381	Intermediate Similarity	NPD7509	Discontinued
0.7349	Intermediate Similarity	NPD7145	Approved
0.7342	Intermediate Similarity	NPD7143	Approved
0.7342	Intermediate Similarity	NPD7144	Approved
0.7284	Intermediate Similarity	NPD4785	Approved
0.7284	Intermediate Similarity	NPD4784	Approved
0.7273	Intermediate Similarity	NPD3618	Phase 1
0.725	Intermediate Similarity	NPD4243	Approved
0.7222	Intermediate Similarity	NPD5328	Approved
0.7191	Intermediate Similarity	NPD7524	Approved
0.7191	Intermediate Similarity	NPD7750	Discontinued
0.7176	Intermediate Similarity	NPD4748	Discontinued
0.7159	Intermediate Similarity	NPD6893	Approved
0.7093	Intermediate Similarity	NPD6898	Phase 1
0.7083	Intermediate Similarity	NPD7640	Approved
0.7083	Intermediate Similarity	NPD7639	Approved
0.7065	Intermediate Similarity	NPD7515	Phase 2
0.7065	Intermediate Similarity	NPD6079	Approved
0.7045	Intermediate Similarity	NPD3665	Phase 1
0.7045	Intermediate Similarity	NPD3133	Approved
0.7045	Intermediate Similarity	NPD3666	Approved
0.7024	Intermediate Similarity	NPD6932	Approved
0.6989	Remote Similarity	NPD6399	Phase 3
0.6979	Remote Similarity	NPD4225	Approved
0.6979	Remote Similarity	NPD7638	Approved
0.6974	Remote Similarity	NPD368	Approved
0.6915	Remote Similarity	NPD7748	Approved
0.6882	Remote Similarity	NPD7087	Discontinued
0.686	Remote Similarity	NPD6683	Phase 2
0.6854	Remote Similarity	NPD3668	Phase 3
0.6849	Remote Similarity	NPD342	Phase 1
0.6837	Remote Similarity	NPD4159	Approved
0.6809	Remote Similarity	NPD4202	Approved
0.6786	Remote Similarity	NPD5275	Approved
0.6786	Remote Similarity	NPD4190	Phase 3
0.6782	Remote Similarity	NPD4695	Discontinued
0.6729	Remote Similarity	NPD7115	Discovery
0.6703	Remote Similarity	NPD4623	Approved
0.6703	Remote Similarity	NPD5279	Phase 3
0.6703	Remote Similarity	NPD4519	Discontinued
0.6702	Remote Similarity	NPD7637	Suspended
0.6702	Remote Similarity	NPD6411	Approved
0.6701	Remote Similarity	NPD7902	Approved
0.6667	Remote Similarity	NPD4195	Approved
0.6667	Remote Similarity	NPD6051	Approved
0.6632	Remote Similarity	NPD5778	Approved
0.6632	Remote Similarity	NPD5779	Approved
0.66	Remote Similarity	NPD5211	Phase 2
0.6598	Remote Similarity	NPD5221	Approved
0.6598	Remote Similarity	NPD4697	Phase 3
0.6598	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD5222	Approved
0.6593	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD1696	Phase 3
0.6533	Remote Similarity	NPD4219	Approved
0.6531	Remote Similarity	NPD5173	Approved
0.6531	Remote Similarity	NPD4755	Approved
0.6522	Remote Similarity	NPD6409	Approved
0.6522	Remote Similarity	NPD5330	Approved
0.6522	Remote Similarity	NPD7146	Approved
0.6522	Remote Similarity	NPD7334	Approved
0.6522	Remote Similarity	NPD6684	Approved
0.6522	Remote Similarity	NPD7521	Approved
0.65	Remote Similarity	NPD5344	Discontinued
0.6489	Remote Similarity	NPD6101	Approved
0.6489	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD4753	Phase 2
0.6484	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD5141	Approved
0.6465	Remote Similarity	NPD5290	Discontinued
0.6444	Remote Similarity	NPD4223	Phase 3
0.6444	Remote Similarity	NPD4221	Approved
0.6436	Remote Similarity	NPD7632	Discontinued
0.6421	Remote Similarity	NPD7136	Phase 2
0.6413	Remote Similarity	NPD5329	Approved
0.6408	Remote Similarity	NPD6402	Approved
0.6408	Remote Similarity	NPD7128	Approved
0.6408	Remote Similarity	NPD5739	Approved
0.6408	Remote Similarity	NPD6675	Approved
0.6404	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.64	Remote Similarity	NPD5285	Approved
0.64	Remote Similarity	NPD4700	Approved
0.64	Remote Similarity	NPD5286	Approved
0.64	Remote Similarity	NPD4696	Approved
0.6392	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD7900	Approved
0.6383	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD6903	Approved
0.6364	Remote Similarity	NPD6084	Phase 2
0.6364	Remote Similarity	NPD6083	Phase 2
0.6353	Remote Similarity	NPD4732	Discontinued
0.6337	Remote Similarity	NPD5223	Approved
0.6304	Remote Similarity	NPD4197	Approved
0.6286	Remote Similarity	NPD7320	Approved
0.6286	Remote Similarity	NPD6899	Approved
0.6286	Remote Similarity	NPD6881	Approved
0.6275	Remote Similarity	NPD5225	Approved
0.6275	Remote Similarity	NPD4633	Approved
0.6275	Remote Similarity	NPD5224	Approved
0.6275	Remote Similarity	NPD5226	Approved
0.6264	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6238	Remote Similarity	NPD6648	Approved
0.6226	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6226	Remote Similarity	NPD6372	Approved
0.6226	Remote Similarity	NPD6373	Approved
0.6214	Remote Similarity	NPD4754	Approved
0.6214	Remote Similarity	NPD5174	Approved
0.6214	Remote Similarity	NPD5175	Approved
0.6211	Remote Similarity	NPD6672	Approved
0.6211	Remote Similarity	NPD5737	Approved
0.6196	Remote Similarity	NPD5362	Discontinued
0.6196	Remote Similarity	NPD4788	Approved
0.619	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.619	Remote Similarity	NPD5697	Approved
0.619	Remote Similarity	NPD5701	Approved
0.6186	Remote Similarity	NPD8034	Phase 2
0.6186	Remote Similarity	NPD8035	Phase 2
0.618	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.618	Remote Similarity	NPD3617	Approved
0.617	Remote Similarity	NPD4688	Approved
0.617	Remote Similarity	NPD4690	Approved
0.617	Remote Similarity	NPD4693	Phase 3
0.617	Remote Similarity	NPD4689	Approved
0.617	Remote Similarity	NPD5205	Approved
0.617	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.617	Remote Similarity	NPD4138	Approved
0.6168	Remote Similarity	NPD7102	Approved
0.6168	Remote Similarity	NPD7290	Approved
0.6168	Remote Similarity	NPD6883	Approved
0.6162	Remote Similarity	NPD5210	Approved
0.6162	Remote Similarity	NPD4629	Approved
0.6146	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6132	Remote Similarity	NPD6011	Approved
0.6132	Remote Similarity	NPD6686	Approved
0.6118	Remote Similarity	NPD4787	Phase 1
0.6111	Remote Similarity	NPD6847	Approved
0.6111	Remote Similarity	NPD8130	Phase 1
0.6111	Remote Similarity	NPD6649	Approved
0.6111	Remote Similarity	NPD6869	Approved
0.6111	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD6650	Approved
0.6111	Remote Similarity	NPD6617	Approved
0.6105	Remote Similarity	NPD3573	Approved
0.6095	Remote Similarity	NPD4767	Approved
0.6095	Remote Similarity	NPD6008	Approved
0.6095	Remote Similarity	NPD4768	Approved
0.6095	Remote Similarity	NPD6640	Phase 3
0.6082	Remote Similarity	NPD3168	Discontinued
0.6075	Remote Similarity	NPD6013	Approved
0.6075	Remote Similarity	NPD6014	Approved
0.6075	Remote Similarity	NPD6012	Approved
0.6055	Remote Similarity	NPD8297	Approved
0.6055	Remote Similarity	NPD6882	Approved
0.6047	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6047	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6044	Remote Similarity	NPD4821	Approved
0.6044	Remote Similarity	NPD4820	Approved
0.6044	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6044	Remote Similarity	NPD4819	Approved
0.6044	Remote Similarity	NPD4822	Approved
0.6042	Remote Similarity	NPD4722	Approved
0.6042	Remote Similarity	NPD4723	Approved
0.6038	Remote Similarity	NPD6412	Phase 2
0.6022	Remote Similarity	NPD5332	Approved
0.6022	Remote Similarity	NPD7154	Phase 3
0.6022	Remote Similarity	NPD5331	Approved
0.6019	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5695	Phase 3
0.6	Remote Similarity	NPD4271	Approved
0.6	Remote Similarity	NPD4268	Approved
0.6	Remote Similarity	NPD6098	Approved
0.6	Remote Similarity	NPD3699	Clinical (unspecified phase)

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