NPASS Compound

Structure

NPC476177 OpenBabel07101718182D 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 0 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 2 0 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:	302.22
Volume:	332.558
LogP:	4.821
LogD:	4.031
LogS:	-5.506
# Rotatable Bonds:	1
TPSA:	29.6
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.666
Synthetic Accessibility Score:	4.514
Fsp3:	0.85
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:	-4.799
MDCK Permeability:	2.5170689696096815e-05
Pgp-inhibitor:	0.996
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.234
30% Bioavailability (F30%):	0.126

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.1
Plasma Protein Binding (PPB):	90.24822998046875%
Volume Distribution (VD):	0.671
Pgp-substrate:	12.073115348815918%

ADMET: Metabolism

CYP1A2-inhibitor:	0.051
CYP1A2-substrate:	0.588
CYP2C19-inhibitor:	0.216
CYP2C19-substrate:	0.816
CYP2C9-inhibitor:	0.282
CYP2C9-substrate:	0.035
CYP2D6-inhibitor:	0.045
CYP2D6-substrate:	0.126
CYP3A4-inhibitor:	0.805
CYP3A4-substrate:	0.402

ADMET: Excretion

Clearance (CL):	12.76
Half-life (T1/2):	0.103

ADMET: Toxicity

hERG Blockers:	0.042
Human Hepatotoxicity (H-HT):	0.48
Drug-inuced Liver Injury (DILI):	0.053
AMES Toxicity:	0.02
Rat Oral Acute Toxicity:	0.66
Maximum Recommended Daily Dose:	0.899
Skin Sensitization:	0.842
Carcinogencity:	0.654
Eye Corrosion:	0.414
Eye Irritation:	0.789
Respiratory Toxicity:	0.979

Download Data

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

Natural Product: NPC476177

Natural Product ID:	NPC476177
*Common Name:**	Rel-15(Zeta),16-Epoxy-7-Oxopimar-8,14-Ene
IUPAC Name:	(4aS,4bR,7S,10aS)-1,1,4a,7-tetramethyl-7-(oxiran-2-yl)-2,3,4,4b,5,6,10,10a-octahydrophenanthren-9-one
Synonyms:
Standard InCHIKey:	AZVDGFALOQJRGB-BNERGVSPSA-N
Standard InCHI:	InChI=1S/C20H30O2/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/h11,14,16-17H,5-10,12H2,1-4H3/t14-,16-,17?,19-,20+/m0/s1
SMILES:	CC1(CCCC2(C1CC(=O)C3=CC(CCC32)(C)C4CO4)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL551467
PubChem CID:	44179876
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	3

Activity Type	# Activity
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1176	Organism	Mycobacterium fortuitum	Mycobacterium fortuitum	MIC	=	128.0	ug.mL-1	PMID[555701]
NPT1177	Organism	Mycobacterium phlei	Mycobacterium phlei	MIC	=	64.0	ug.mL-1	PMID[555701]
NPT602	Organism	Mycobacterium smegmatis	Mycobacterium smegmatis	MIC	=	128.0	ug.mL-1	PMID[555701]

☑ 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 NPC476177 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	207
0.1-0.2	1375
0.2-0.3	5851
0.3-0.4	15531
0.4-0.5	8315
0.5-0.6	6453
0.6-0.7	3973
0.7-0.8	966
0.8-0.85	23
0.85-0.9	2
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8701	High Similarity	NPC472300
0.8608	High Similarity	NPC2482
0.8537	High Similarity	NPC133652
0.85	High Similarity	NPC474085
0.85	High Similarity	NPC121984
0.85	High Similarity	NPC149237
0.8333	Intermediate Similarity	NPC470525
0.8313	Intermediate Similarity	NPC323765
0.8313	Intermediate Similarity	NPC6185
0.8313	Intermediate Similarity	NPC476678
0.8313	Intermediate Similarity	NPC241512
0.8272	Intermediate Similarity	NPC14151
0.8256	Intermediate Similarity	NPC475823
0.8256	Intermediate Similarity	NPC474209
0.8228	Intermediate Similarity	NPC165711
0.8214	Intermediate Similarity	NPC31564
0.8214	Intermediate Similarity	NPC145879
0.8214	Intermediate Similarity	NPC474732
0.8214	Intermediate Similarity	NPC195640
0.8214	Intermediate Similarity	NPC474778
0.8214	Intermediate Similarity	NPC474733
0.8214	Intermediate Similarity	NPC94666
0.8214	Intermediate Similarity	NPC472974
0.8193	Intermediate Similarity	NPC85774
0.8193	Intermediate Similarity	NPC58841
0.8193	Intermediate Similarity	NPC161423
0.8193	Intermediate Similarity	NPC227064
0.8193	Intermediate Similarity	NPC476412
0.8193	Intermediate Similarity	NPC214043
0.8193	Intermediate Similarity	NPC321187
0.8193	Intermediate Similarity	NPC329043
0.8171	Intermediate Similarity	NPC151519
0.8171	Intermediate Similarity	NPC470813
0.8171	Intermediate Similarity	NPC212083
0.8171	Intermediate Similarity	NPC163236
0.8171	Intermediate Similarity	NPC328351
0.8171	Intermediate Similarity	NPC103486
0.8148	Intermediate Similarity	NPC108955
0.8148	Intermediate Similarity	NPC472478
0.8148	Intermediate Similarity	NPC476809
0.814	Intermediate Similarity	NPC119416
0.8133	Intermediate Similarity	NPC155198
0.8125	Intermediate Similarity	NPC62336
0.8125	Intermediate Similarity	NPC475994
0.8118	Intermediate Similarity	NPC58063
0.8118	Intermediate Similarity	NPC475740
0.8101	Intermediate Similarity	NPC263582
0.8095	Intermediate Similarity	NPC470574
0.8095	Intermediate Similarity	NPC8518
0.8095	Intermediate Similarity	NPC263997
0.8095	Intermediate Similarity	NPC476426
0.8095	Intermediate Similarity	NPC132228
0.8095	Intermediate Similarity	NPC469948
0.8095	Intermediate Similarity	NPC474680
0.8077	Intermediate Similarity	NPC167049
0.8077	Intermediate Similarity	NPC166797
0.8077	Intermediate Similarity	NPC469691
0.8072	Intermediate Similarity	NPC470047
0.8072	Intermediate Similarity	NPC470046
0.8049	Intermediate Similarity	NPC278459
0.8049	Intermediate Similarity	NPC116797
0.8049	Intermediate Similarity	NPC475665
0.8049	Intermediate Similarity	NPC90055
0.8049	Intermediate Similarity	NPC55869
0.8025	Intermediate Similarity	NPC308038
0.8025	Intermediate Similarity	NPC283789
0.8023	Intermediate Similarity	NPC158778
0.8023	Intermediate Similarity	NPC206060
0.8	Intermediate Similarity	NPC327115
0.8	Intermediate Similarity	NPC472985
0.8	Intermediate Similarity	NPC472986
0.8	Intermediate Similarity	NPC197659
0.7976	Intermediate Similarity	NPC221758
0.7976	Intermediate Similarity	NPC25833
0.7976	Intermediate Similarity	NPC180834
0.7976	Intermediate Similarity	NPC237712
0.7976	Intermediate Similarity	NPC473246
0.7976	Intermediate Similarity	NPC312660
0.7976	Intermediate Similarity	NPC472265
0.7976	Intermediate Similarity	NPC59453
0.7975	Intermediate Similarity	NPC469678
0.7975	Intermediate Similarity	NPC469669
0.7975	Intermediate Similarity	NPC475771
0.7975	Intermediate Similarity	NPC114236
0.7955	Intermediate Similarity	NPC131872
0.7955	Intermediate Similarity	NPC472975
0.7955	Intermediate Similarity	NPC26865
0.7955	Intermediate Similarity	NPC218301
0.7952	Intermediate Similarity	NPC302661
0.7952	Intermediate Similarity	NPC238991
0.7952	Intermediate Similarity	NPC93590
0.7952	Intermediate Similarity	NPC48362
0.7952	Intermediate Similarity	NPC310989
0.7952	Intermediate Similarity	NPC142683
0.7952	Intermediate Similarity	NPC100297
0.7931	Intermediate Similarity	NPC186688
0.7931	Intermediate Similarity	NPC26959
0.7931	Intermediate Similarity	NPC31985
0.7931	Intermediate Similarity	NPC469546
0.7931	Intermediate Similarity	NPC477973
0.7931	Intermediate Similarity	NPC1015
0.7931	Intermediate Similarity	NPC472973
0.7931	Intermediate Similarity	NPC268406
0.7927	Intermediate Similarity	NPC474956
0.7927	Intermediate Similarity	NPC267517
0.7922	Intermediate Similarity	NPC2634
0.7922	Intermediate Similarity	NPC265782
0.7922	Intermediate Similarity	NPC251929
0.7912	Intermediate Similarity	NPC151488
0.7907	Intermediate Similarity	NPC93778
0.7901	Intermediate Similarity	NPC189485
0.7901	Intermediate Similarity	NPC59436
0.7901	Intermediate Similarity	NPC35574
0.7901	Intermediate Similarity	NPC469996
0.7895	Intermediate Similarity	NPC188292
0.7895	Intermediate Similarity	NPC260474
0.7882	Intermediate Similarity	NPC189311
0.7882	Intermediate Similarity	NPC300985
0.7882	Intermediate Similarity	NPC2709
0.7865	Intermediate Similarity	NPC229976
0.7865	Intermediate Similarity	NPC79117
0.7865	Intermediate Similarity	NPC474736
0.7865	Intermediate Similarity	NPC109305
0.7857	Intermediate Similarity	NPC193198
0.7857	Intermediate Similarity	NPC102197
0.7857	Intermediate Similarity	NPC307258
0.7857	Intermediate Similarity	NPC105803
0.7841	Intermediate Similarity	NPC223093
0.7841	Intermediate Similarity	NPC85173
0.7841	Intermediate Similarity	NPC328141
0.7841	Intermediate Similarity	NPC48010
0.7831	Intermediate Similarity	NPC136150
0.7831	Intermediate Similarity	NPC3915
0.7831	Intermediate Similarity	NPC473217
0.7831	Intermediate Similarity	NPC471898
0.7831	Intermediate Similarity	NPC225515
0.7831	Intermediate Similarity	NPC474955
0.7821	Intermediate Similarity	NPC54123
0.7816	Intermediate Similarity	NPC328539
0.7816	Intermediate Similarity	NPC471722
0.7816	Intermediate Similarity	NPC474677
0.7816	Intermediate Similarity	NPC215831
0.7816	Intermediate Similarity	NPC472802
0.7805	Intermediate Similarity	NPC472490
0.7805	Intermediate Similarity	NPC474113
0.7802	Intermediate Similarity	NPC471775
0.7792	Intermediate Similarity	NPC139397
0.7791	Intermediate Similarity	NPC470050
0.7791	Intermediate Similarity	NPC20688
0.7791	Intermediate Similarity	NPC194417
0.7791	Intermediate Similarity	NPC179591
0.7791	Intermediate Similarity	NPC222613
0.7791	Intermediate Similarity	NPC51014
0.7791	Intermediate Similarity	NPC470955
0.7791	Intermediate Similarity	NPC475022
0.7791	Intermediate Similarity	NPC158393
0.7791	Intermediate Similarity	NPC220478
0.7791	Intermediate Similarity	NPC264127
0.7791	Intermediate Similarity	NPC118648
0.7791	Intermediate Similarity	NPC470051
0.7778	Intermediate Similarity	NPC97377
0.7778	Intermediate Similarity	NPC74995
0.7778	Intermediate Similarity	NPC472976
0.7778	Intermediate Similarity	NPC38830
0.7778	Intermediate Similarity	NPC23170
0.7778	Intermediate Similarity	NPC472977
0.7765	Intermediate Similarity	NPC82902
0.7765	Intermediate Similarity	NPC33913
0.7753	Intermediate Similarity	NPC272746
0.7753	Intermediate Similarity	NPC49420
0.7753	Intermediate Similarity	NPC262870
0.7753	Intermediate Similarity	NPC190442
0.7753	Intermediate Similarity	NPC472978
0.7738	Intermediate Similarity	NPC178676
0.7738	Intermediate Similarity	NPC70479
0.7738	Intermediate Similarity	NPC321289
0.7738	Intermediate Similarity	NPC200513
0.7738	Intermediate Similarity	NPC193347
0.7738	Intermediate Similarity	NPC327969
0.7727	Intermediate Similarity	NPC309603
0.7727	Intermediate Similarity	NPC477943
0.7727	Intermediate Similarity	NPC50070
0.7727	Intermediate Similarity	NPC184663
0.7727	Intermediate Similarity	NPC73995
0.7727	Intermediate Similarity	NPC473999
0.7722	Intermediate Similarity	NPC474228
0.7722	Intermediate Similarity	NPC303613
0.7722	Intermediate Similarity	NPC107783
0.7722	Intermediate Similarity	NPC92909
0.7717	Intermediate Similarity	NPC226986
0.7711	Intermediate Similarity	NPC172013
0.7711	Intermediate Similarity	NPC469637
0.7703	Intermediate Similarity	NPC197238
0.7703	Intermediate Similarity	NPC202118
0.7701	Intermediate Similarity	NPC73064
0.7701	Intermediate Similarity	NPC298904
0.7701	Intermediate Similarity	NPC30421
0.7701	Intermediate Similarity	NPC470523
0.7701	Intermediate Similarity	NPC38885
0.7701	Intermediate Similarity	NPC477228

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 NPC476177 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	196
0.1-0.2	1647
0.2-0.3	4115
0.3-0.4	2254
0.4-0.5	552
0.5-0.6	158
0.6-0.7	166
0.7-0.8	61
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8375	Intermediate Similarity	NPD4695	Discontinued
0.8214	Intermediate Similarity	NPD7521	Approved
0.8214	Intermediate Similarity	NPD7334	Approved
0.8214	Intermediate Similarity	NPD5330	Approved
0.8214	Intermediate Similarity	NPD7146	Approved
0.8214	Intermediate Similarity	NPD6409	Approved
0.8214	Intermediate Similarity	NPD6684	Approved
0.8193	Intermediate Similarity	NPD3666	Approved
0.8193	Intermediate Similarity	NPD3133	Approved
0.8193	Intermediate Similarity	NPD3665	Phase 1
0.8171	Intermediate Similarity	NPD3667	Approved
0.8023	Intermediate Similarity	NPD6903	Approved
0.8023	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD3618	Phase 1
0.7976	Intermediate Similarity	NPD3668	Phase 3
0.7976	Intermediate Similarity	NPD4786	Approved
0.7922	Intermediate Similarity	NPD4691	Approved
0.7816	Intermediate Similarity	NPD6672	Approved
0.7816	Intermediate Similarity	NPD5737	Approved
0.7792	Intermediate Similarity	NPD4137	Phase 3
0.7791	Intermediate Similarity	NPD5279	Phase 3
0.7753	Intermediate Similarity	NPD6079	Approved
0.7738	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7738	Intermediate Similarity	NPD4223	Phase 3
0.7738	Intermediate Similarity	NPD4221	Approved
0.7727	Intermediate Similarity	NPD5328	Approved
0.7701	Intermediate Similarity	NPD3573	Approved
0.7692	Intermediate Similarity	NPD4747	Approved
0.7625	Intermediate Similarity	NPD4058	Approved
0.7582	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD7900	Approved
0.7582	Intermediate Similarity	NPD7748	Approved
0.7558	Intermediate Similarity	NPD4197	Approved
0.7556	Intermediate Similarity	NPD7515	Phase 2
0.7528	Intermediate Similarity	NPD4753	Phase 2
0.7473	Intermediate Similarity	NPD6399	Phase 3
0.7473	Intermediate Similarity	NPD4202	Approved
0.7471	Intermediate Similarity	NPD5329	Approved
0.747	Intermediate Similarity	NPD3617	Approved
0.7419	Intermediate Similarity	NPD5222	Approved
0.7419	Intermediate Similarity	NPD5221	Approved
0.7419	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7416	Intermediate Similarity	NPD5208	Approved
0.7386	Intermediate Similarity	NPD4519	Discontinued
0.7386	Intermediate Similarity	NPD4688	Approved
0.7386	Intermediate Similarity	NPD5205	Approved
0.7386	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD4690	Approved
0.7386	Intermediate Similarity	NPD4623	Approved
0.7386	Intermediate Similarity	NPD4689	Approved
0.7386	Intermediate Similarity	NPD4693	Phase 3
0.7386	Intermediate Similarity	NPD5690	Phase 2
0.7386	Intermediate Similarity	NPD4138	Approved
0.7375	Intermediate Similarity	NPD5276	Approved
0.7347	Intermediate Similarity	NPD6008	Approved
0.734	Intermediate Similarity	NPD5173	Approved
0.734	Intermediate Similarity	NPD7902	Approved
0.7333	Intermediate Similarity	NPD6904	Approved
0.7333	Intermediate Similarity	NPD6080	Approved
0.7333	Intermediate Similarity	NPD6673	Approved
0.7312	Intermediate Similarity	NPD5210	Approved
0.7312	Intermediate Similarity	NPD4629	Approved
0.7312	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD1694	Approved
0.7234	Intermediate Similarity	NPD4697	Phase 3
0.7215	Intermediate Similarity	NPD3621	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD6001	Approved
0.7195	Intermediate Similarity	NPD4687	Approved
0.7195	Intermediate Similarity	NPD5733	Approved
0.7191	Intermediate Similarity	NPD4694	Approved
0.7191	Intermediate Similarity	NPD6098	Approved
0.7191	Intermediate Similarity	NPD5280	Approved
0.7188	Intermediate Similarity	NPD5286	Approved
0.7188	Intermediate Similarity	NPD5285	Approved
0.7188	Intermediate Similarity	NPD4696	Approved
0.7176	Intermediate Similarity	NPD4195	Approved
0.7174	Intermediate Similarity	NPD5693	Phase 1
0.7158	Intermediate Similarity	NPD6083	Phase 2
0.7158	Intermediate Similarity	NPD4755	Approved
0.7158	Intermediate Similarity	NPD6084	Phase 2
0.7143	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD5695	Phase 3
0.7113	Intermediate Similarity	NPD5223	Approved
0.7083	Intermediate Similarity	NPD5696	Approved
0.7065	Intermediate Similarity	NPD5692	Phase 3
0.7065	Intermediate Similarity	NPD5207	Approved
0.7053	Intermediate Similarity	NPD7732	Phase 3
0.7045	Intermediate Similarity	NPD4788	Approved
0.7041	Intermediate Similarity	NPD5224	Approved
0.7041	Intermediate Similarity	NPD5211	Phase 2
0.7041	Intermediate Similarity	NPD4633	Approved
0.7041	Intermediate Similarity	NPD5225	Approved
0.7041	Intermediate Similarity	NPD5226	Approved
0.7024	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD4700	Approved
0.6989	Remote Similarity	NPD6050	Approved
0.6989	Remote Similarity	NPD5694	Approved
0.697	Remote Similarity	NPD5174	Approved
0.697	Remote Similarity	NPD5175	Approved
0.6931	Remote Similarity	NPD5697	Approved
0.6905	Remote Similarity	NPD6942	Approved
0.6905	Remote Similarity	NPD7339	Approved
0.69	Remote Similarity	NPD5141	Approved
0.6882	Remote Similarity	NPD4096	Approved
0.6863	Remote Similarity	NPD6899	Approved
0.6863	Remote Similarity	NPD6011	Approved
0.6863	Remote Similarity	NPD6881	Approved
0.6848	Remote Similarity	NPD4518	Approved
0.6832	Remote Similarity	NPD6675	Approved
0.6832	Remote Similarity	NPD5739	Approved
0.6832	Remote Similarity	NPD7128	Approved
0.6832	Remote Similarity	NPD6402	Approved
0.6822	Remote Similarity	NPD7115	Discovery
0.6818	Remote Similarity	NPD8028	Phase 2
0.6809	Remote Similarity	NPD5281	Approved
0.6809	Remote Similarity	NPD5284	Approved
0.6809	Remote Similarity	NPD6411	Approved
0.68	Remote Similarity	NPD4754	Approved
0.6796	Remote Similarity	NPD6014	Approved
0.6796	Remote Similarity	NPD6012	Approved
0.6796	Remote Similarity	NPD6013	Approved
0.6782	Remote Similarity	NPD7645	Phase 2
0.6765	Remote Similarity	NPD6412	Phase 2
0.6765	Remote Similarity	NPD5701	Approved
0.675	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.675	Remote Similarity	NPD7331	Phase 2
0.6737	Remote Similarity	NPD5133	Approved
0.6731	Remote Similarity	NPD7102	Approved
0.6731	Remote Similarity	NPD6883	Approved
0.6731	Remote Similarity	NPD7290	Approved
0.6711	Remote Similarity	NPD287	Approved
0.6705	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD7614	Phase 1
0.6699	Remote Similarity	NPD7320	Approved
0.6699	Remote Similarity	NPD5168	Approved
0.6699	Remote Similarity	NPD5128	Approved
0.6699	Remote Similarity	NPD4729	Approved
0.6699	Remote Similarity	NPD4730	Approved
0.6667	Remote Similarity	NPD4767	Approved
0.6667	Remote Similarity	NPD8130	Phase 1
0.6667	Remote Similarity	NPD6649	Approved
0.6667	Remote Similarity	NPD6650	Approved
0.6667	Remote Similarity	NPD6847	Approved
0.6667	Remote Similarity	NPD3527	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6617	Approved
0.6667	Remote Similarity	NPD4768	Approved
0.6667	Remote Similarity	NPD6869	Approved
0.6635	Remote Similarity	NPD6372	Approved
0.6635	Remote Similarity	NPD6373	Approved
0.6633	Remote Similarity	NPD5959	Approved
0.6629	Remote Similarity	NPD4692	Approved
0.6629	Remote Similarity	NPD4139	Approved
0.6625	Remote Similarity	NPD7341	Phase 2
0.6604	Remote Similarity	NPD6882	Approved
0.6604	Remote Similarity	NPD8297	Approved
0.6598	Remote Similarity	NPD5654	Approved
0.6596	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD6101	Approved
0.6588	Remote Similarity	NPD6924	Approved
0.6588	Remote Similarity	NPD6926	Approved
0.6571	Remote Similarity	NPD5248	Approved
0.6571	Remote Similarity	NPD4634	Approved
0.6571	Remote Similarity	NPD5250	Approved
0.6571	Remote Similarity	NPD5169	Approved
0.6571	Remote Similarity	NPD5247	Approved
0.6571	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD5249	Phase 3
0.6571	Remote Similarity	NPD5135	Approved
0.6571	Remote Similarity	NPD5251	Approved
0.6566	Remote Similarity	NPD7638	Approved
0.6566	Remote Similarity	NPD4225	Approved
0.6542	Remote Similarity	NPD4632	Approved
0.6538	Remote Similarity	NPD6686	Approved
0.6535	Remote Similarity	NPD5091	Approved
0.6522	Remote Similarity	NPD1696	Phase 3
0.6522	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD8039	Approved
0.6509	Remote Similarity	NPD5217	Approved
0.6509	Remote Similarity	NPD5127	Approved
0.6509	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD5216	Approved
0.6509	Remote Similarity	NPD5215	Approved
0.65	Remote Similarity	NPD7639	Approved
0.65	Remote Similarity	NPD7640	Approved
0.6495	Remote Similarity	NPD5282	Discontinued
0.6471	Remote Similarity	NPD6052	Approved
0.6442	Remote Similarity	NPD6614	Approved
0.6442	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6437	Remote Similarity	NPD6933	Approved
0.6422	Remote Similarity	NPD6868	Approved
0.6422	Remote Similarity	NPD6274	Approved
0.6421	Remote Similarity	NPD6051	Approved
0.64	Remote Similarity	NPD5290	Discontinued
0.6395	Remote Similarity	NPD4784	Approved
0.6395	Remote Similarity	NPD4785	Approved
0.6389	Remote Similarity	NPD6858	Approved
0.6389	Remote Similarity	NPD7094	Approved
0.6375	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD5209	Approved
0.6364	Remote Similarity	NPD6317	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