NPASS Compound

Structure

NPC310992 OpenBabel07101719242D 21 23 0 0 1 0 0 0 0 0999 V2000 4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2321 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7321 -0.0000 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 -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 0.0000 2.0000 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 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 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 0.8660 1.5000 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 -0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 2.0000 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 -0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 2 13 1 0 0 0 0 3 19 1 0 0 0 0 4 19 1 0 0 0 0 6 11 1 0 0 0 0 6 12 1 0 0 0 0 7 9 1 0 0 0 0 7 14 2 0 0 0 0 8 10 1 0 0 0 0 8 15 2 0 0 0 0 9 16 2 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 1 0 0 0 0 14 18 1 0 0 0 0 15 16 1 0 0 0 0 15 18 1 0 0 0 0 16 20 1 0 0 0 0 17 19 1 0 0 0 0 17 20 1 6 0 0 0 18 21 2 0 0 0 0 20 5 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	284.21
Volume:	327.051
LogP:	6.092
LogD:	4.693
LogS:	-5.746
# Rotatable Bonds:	1
TPSA:	20.23
# H-Bond Aceptor:	1
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.709
Synthetic Accessibility Score:	3.848
Fsp3:	0.6
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:	-4.847
MDCK Permeability:	1.9629345842986368e-05
Pgp-inhibitor:	0.993
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.552
30% Bioavailability (F30%):	0.972

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.052
Plasma Protein Binding (PPB):	99.20476531982422%
Volume Distribution (VD):	4.269
Pgp-substrate:	2.2277026176452637%

ADMET: Metabolism

CYP1A2-inhibitor:	0.648
CYP1A2-substrate:	0.746
CYP2C19-inhibitor:	0.592
CYP2C19-substrate:	0.911
CYP2C9-inhibitor:	0.401
CYP2C9-substrate:	0.876
CYP2D6-inhibitor:	0.734
CYP2D6-substrate:	0.81
CYP3A4-inhibitor:	0.756
CYP3A4-substrate:	0.624

ADMET: Excretion

Clearance (CL):	7.304
Half-life (T1/2):	0.035

ADMET: Toxicity

hERG Blockers:	0.158
Human Hepatotoxicity (H-HT):	0.248
Drug-inuced Liver Injury (DILI):	0.045
AMES Toxicity:	0.036
Rat Oral Acute Toxicity:	0.739
Maximum Recommended Daily Dose:	0.929
Skin Sensitization:	0.932
Carcinogencity:	0.766
Eye Corrosion:	0.009
Eye Irritation:	0.892
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: NPC310992

Natural Product ID:	NPC310992
*Common Name:**	Deoxybuddlejone
IUPAC Name:	(4bS,8aS)-4b,8,8-trimethyl-2-propan-2-yl-6,7,8a,9-tetrahydro-5H-phenanthren-1-one
Synonyms:	Deoxybuddlejone
Standard InCHIKey:	LIYZCWXRVNEQMR-FXAWDEMLSA-N
Standard InCHI:	InChI=1S/C20H28O/c1-13(2)14-7-9-16-15(18(14)21)8-10-17-19(3,4)11-6-12-20(16,17)5/h7-9,13,17H,6,10-12H2,1-5H3/t17-,20+/m0/s1
SMILES:	CC(C1=CC=C2C(=CC[C@@H]3[C@]2(C)CCCC3(C)C)C1=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL506233
PubChem CID:	10334095
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
NPO27625	Buddleja globosa	Species	Scrophulariaceae	Eukaryota	Roots	London	n.a.	PMID[10514305]
NPO27625	Buddleja globosa	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11000021]
NPO27625	Buddleja globosa	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27625	Buddleja globosa	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]

☑ 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
NPT328	Organism	Epidermophyton floccosum	Epidermophyton floccosum	MIC	=	2640000.0	nM	PMID[504802]
NPT329	Organism	Trichophyton rubrum	Trichophyton rubrum	MIC	=	2640000.0	nM	PMID[504802]
NPT4353	Organism	Trichophyton interdigitale	Trichophyton interdigitale	MIC	=	2640000.0	nM	PMID[504802]

☑ 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 NPC310992 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	270
0.1-0.2	1928
0.2-0.3	10470
0.3-0.4	16121
0.4-0.5	8185
0.5-0.6	4121
0.6-0.7	1274
0.7-0.8	273
0.8-0.85	40
0.85-0.9	12
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9385	High Similarity	NPC260474
0.9385	High Similarity	NPC188292
0.9091	High Similarity	NPC87141
0.8923	High Similarity	NPC251118
0.8889	High Similarity	NPC127582
0.8841	High Similarity	NPC470045
0.8841	High Similarity	NPC470044
0.8824	High Similarity	NPC251929
0.8824	High Similarity	NPC265782
0.8824	High Similarity	NPC2634
0.8769	High Similarity	NPC285371
0.8769	High Similarity	NPC469662
0.8769	High Similarity	NPC475124
0.875	High Similarity	NPC189485
0.873	High Similarity	NPC472304
0.873	High Similarity	NPC276764
0.8696	High Similarity	NPC54123
0.8676	High Similarity	NPC256846
0.8676	High Similarity	NPC139397
0.8657	High Similarity	NPC193770
0.863	High Similarity	NPC27817
0.863	High Similarity	NPC170793
0.8615	High Similarity	NPC288253
0.8615	High Similarity	NPC202118
0.8615	High Similarity	NPC197238
0.8592	High Similarity	NPC473171
0.8571	High Similarity	NPC251705
0.8571	High Similarity	NPC303613
0.8571	High Similarity	NPC27610
0.8571	High Similarity	NPC474228
0.8571	High Similarity	NPC56905
0.8551	High Similarity	NPC260040
0.8551	High Similarity	NPC282593
0.8551	High Similarity	NPC159577
0.8551	High Similarity	NPC35734
0.8551	High Similarity	NPC307176
0.8529	High Similarity	NPC155198
0.8472	Intermediate Similarity	NPC1254
0.8451	Intermediate Similarity	NPC474796
0.8451	Intermediate Similarity	NPC474797
0.8451	Intermediate Similarity	NPC329866
0.8429	Intermediate Similarity	NPC234707
0.8429	Intermediate Similarity	NPC225467
0.8429	Intermediate Similarity	NPC115023
0.8429	Intermediate Similarity	NPC181204
0.8429	Intermediate Similarity	NPC470078
0.8429	Intermediate Similarity	NPC190035
0.8333	Intermediate Similarity	NPC293803
0.8261	Intermediate Similarity	NPC82477
0.8261	Intermediate Similarity	NPC39157
0.8261	Intermediate Similarity	NPC142754
0.8261	Intermediate Similarity	NPC296697
0.8261	Intermediate Similarity	NPC20610
0.8235	Intermediate Similarity	NPC323005
0.8219	Intermediate Similarity	NPC469793
0.8219	Intermediate Similarity	NPC110725
0.8219	Intermediate Similarity	NPC69408
0.8219	Intermediate Similarity	NPC469796
0.8209	Intermediate Similarity	NPC212210
0.8209	Intermediate Similarity	NPC4638
0.8209	Intermediate Similarity	NPC6697
0.8194	Intermediate Similarity	NPC219232
0.8194	Intermediate Similarity	NPC255021
0.8194	Intermediate Similarity	NPC128346
0.8194	Intermediate Similarity	NPC309852
0.8182	Intermediate Similarity	NPC60565
0.8182	Intermediate Similarity	NPC213152
0.8169	Intermediate Similarity	NPC474562
0.8169	Intermediate Similarity	NPC305501
0.8169	Intermediate Similarity	NPC5701
0.8143	Intermediate Similarity	NPC182815
0.8143	Intermediate Similarity	NPC286814
0.8133	Intermediate Similarity	NPC90965
0.8125	Intermediate Similarity	NPC115385
0.8116	Intermediate Similarity	NPC290350
0.8116	Intermediate Similarity	NPC4370
0.8116	Intermediate Similarity	NPC220210
0.8116	Intermediate Similarity	NPC20181
0.8082	Intermediate Similarity	NPC476346
0.8077	Intermediate Similarity	NPC87552
0.806	Intermediate Similarity	NPC165695
0.8056	Intermediate Similarity	NPC56747
0.8056	Intermediate Similarity	NPC180015
0.8056	Intermediate Similarity	NPC130016
0.8056	Intermediate Similarity	NPC109576
0.8026	Intermediate Similarity	NPC108955
0.8026	Intermediate Similarity	NPC287063
0.8	Intermediate Similarity	NPC311852
0.8	Intermediate Similarity	NPC115515
0.8	Intermediate Similarity	NPC60772
0.8	Intermediate Similarity	NPC308108
0.8	Intermediate Similarity	NPC170799
0.7971	Intermediate Similarity	NPC92327
0.7945	Intermediate Similarity	NPC211641
0.7922	Intermediate Similarity	NPC121984
0.7922	Intermediate Similarity	NPC225515
0.7922	Intermediate Similarity	NPC474085
0.7922	Intermediate Similarity	NPC116797
0.7922	Intermediate Similarity	NPC55869
0.7922	Intermediate Similarity	NPC470034
0.7922	Intermediate Similarity	NPC99308
0.7922	Intermediate Similarity	NPC475833
0.7922	Intermediate Similarity	NPC475863
0.7917	Intermediate Similarity	NPC223187
0.7867	Intermediate Similarity	NPC472300
0.7857	Intermediate Similarity	NPC176107
0.7857	Intermediate Similarity	NPC475523
0.7838	Intermediate Similarity	NPC65650
0.7838	Intermediate Similarity	NPC255650
0.7826	Intermediate Similarity	NPC470329
0.7826	Intermediate Similarity	NPC268039
0.7821	Intermediate Similarity	NPC142253
0.7821	Intermediate Similarity	NPC3511
0.7812	Intermediate Similarity	NPC200258
0.7808	Intermediate Similarity	NPC474488
0.7792	Intermediate Similarity	NPC476809
0.7792	Intermediate Similarity	NPC474509
0.7778	Intermediate Similarity	NPC23117
0.7778	Intermediate Similarity	NPC477856
0.7778	Intermediate Similarity	NPC214770
0.7778	Intermediate Similarity	NPC268564
0.7763	Intermediate Similarity	NPC74410
0.7763	Intermediate Similarity	NPC469996
0.7761	Intermediate Similarity	NPC25853
0.775	Intermediate Similarity	NPC33881
0.7733	Intermediate Similarity	NPC899
0.7733	Intermediate Similarity	NPC180886
0.7733	Intermediate Similarity	NPC309399
0.7727	Intermediate Similarity	NPC266295
0.7727	Intermediate Similarity	NPC30215
0.7727	Intermediate Similarity	NPC94991
0.7722	Intermediate Similarity	NPC118423
0.7722	Intermediate Similarity	NPC102197
0.7714	Intermediate Similarity	NPC176171
0.7703	Intermediate Similarity	NPC20025
0.7692	Intermediate Similarity	NPC6663
0.7692	Intermediate Similarity	NPC4166
0.7692	Intermediate Similarity	NPC278459
0.7683	Intermediate Similarity	NPC72397
0.7671	Intermediate Similarity	NPC21944
0.7671	Intermediate Similarity	NPC133253
0.7662	Intermediate Similarity	NPC472490
0.7662	Intermediate Similarity	NPC476177
0.7656	Intermediate Similarity	NPC5626
0.7639	Intermediate Similarity	NPC474060
0.7632	Intermediate Similarity	NPC165711
0.7612	Intermediate Similarity	NPC259261
0.7612	Intermediate Similarity	NPC96551
0.7612	Intermediate Similarity	NPC285594
0.7595	Intermediate Similarity	NPC311092
0.7595	Intermediate Similarity	NPC469804
0.7595	Intermediate Similarity	NPC469799
0.7595	Intermediate Similarity	NPC469805
0.7595	Intermediate Similarity	NPC469806
0.7595	Intermediate Similarity	NPC472867
0.7595	Intermediate Similarity	NPC103486
0.7595	Intermediate Similarity	NPC268122
0.7595	Intermediate Similarity	NPC472239
0.7576	Intermediate Similarity	NPC192427
0.7564	Intermediate Similarity	NPC26139
0.7564	Intermediate Similarity	NPC472478
0.7564	Intermediate Similarity	NPC469798
0.7564	Intermediate Similarity	NPC2482
0.7564	Intermediate Similarity	NPC469797
0.7561	Intermediate Similarity	NPC136548
0.7536	Intermediate Similarity	NPC472306
0.7536	Intermediate Similarity	NPC167256
0.7536	Intermediate Similarity	NPC32285
0.7534	Intermediate Similarity	NPC40574
0.7534	Intermediate Similarity	NPC246722
0.7534	Intermediate Similarity	NPC151045
0.7532	Intermediate Similarity	NPC4827
0.7532	Intermediate Similarity	NPC471409
0.7532	Intermediate Similarity	NPC275494
0.7531	Intermediate Similarity	NPC132228
0.7531	Intermediate Similarity	NPC8571
0.7531	Intermediate Similarity	NPC133652
0.7531	Intermediate Similarity	NPC263997
0.7531	Intermediate Similarity	NPC8518
0.7531	Intermediate Similarity	NPC474537
0.75	Intermediate Similarity	NPC474790
0.75	Intermediate Similarity	NPC470525
0.75	Intermediate Similarity	NPC49019
0.75	Intermediate Similarity	NPC279639
0.75	Intermediate Similarity	NPC14002
0.75	Intermediate Similarity	NPC41539
0.75	Intermediate Similarity	NPC474976
0.75	Intermediate Similarity	NPC83569
0.75	Intermediate Similarity	NPC19907
0.75	Intermediate Similarity	NPC69898
0.75	Intermediate Similarity	NPC92080
0.75	Intermediate Similarity	NPC112680
0.75	Intermediate Similarity	NPC53733
0.75	Intermediate Similarity	NPC69279
0.75	Intermediate Similarity	NPC295777
0.75	Intermediate Similarity	NPC292589
0.75	Intermediate Similarity	NPC3856
0.75	Intermediate Similarity	NPC37644
0.7468	Intermediate Similarity	NPC473217
0.7468	Intermediate Similarity	NPC149237

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 NPC310992 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	254
0.1-0.2	2046
0.2-0.3	4328
0.3-0.4	1848
0.4-0.5	392
0.5-0.6	181
0.6-0.7	85
0.7-0.8	10
0.8-0.85	3
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8986	High Similarity	NPD4058	Approved
0.8986	High Similarity	NPD5733	Approved
0.8986	High Similarity	NPD4687	Approved
0.8971	High Similarity	NPD5276	Approved
0.8824	High Similarity	NPD4691	Approved
0.8676	High Similarity	NPD4137	Phase 3
0.8551	High Similarity	NPD4747	Approved
0.8261	Intermediate Similarity	NPD3621	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD3527	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD287	Approved
0.7692	Intermediate Similarity	NPD8028	Phase 2
0.7654	Intermediate Similarity	NPD4694	Approved
0.7654	Intermediate Similarity	NPD5280	Approved
0.7564	Intermediate Similarity	NPD4695	Discontinued
0.7439	Intermediate Similarity	NPD5690	Phase 2
0.7439	Intermediate Similarity	NPD5279	Phase 3
0.7375	Intermediate Similarity	NPD4223	Phase 3
0.7375	Intermediate Similarity	NPD4221	Approved
0.7294	Intermediate Similarity	NPD5692	Phase 3
0.7294	Intermediate Similarity	NPD5207	Approved
0.7209	Intermediate Similarity	NPD5284	Approved
0.7209	Intermediate Similarity	NPD5694	Approved
0.7209	Intermediate Similarity	NPD5281	Approved
0.7209	Intermediate Similarity	NPD6050	Approved
0.7195	Intermediate Similarity	NPD3133	Approved
0.7195	Intermediate Similarity	NPD3666	Approved
0.7195	Intermediate Similarity	NPD3665	Phase 1
0.7195	Intermediate Similarity	NPD4197	Approved
0.7176	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3573	Approved
0.7108	Intermediate Similarity	NPD5329	Approved
0.7093	Intermediate Similarity	NPD4096	Approved
0.7089	Intermediate Similarity	NPD3617	Approved
0.7024	Intermediate Similarity	NPD5205	Approved
0.7024	Intermediate Similarity	NPD4688	Approved
0.7024	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD4519	Discontinued
0.7024	Intermediate Similarity	NPD7521	Approved
0.7024	Intermediate Similarity	NPD7334	Approved
0.7024	Intermediate Similarity	NPD6409	Approved
0.7024	Intermediate Similarity	NPD5330	Approved
0.7024	Intermediate Similarity	NPD7146	Approved
0.7024	Intermediate Similarity	NPD4689	Approved
0.7024	Intermediate Similarity	NPD4623	Approved
0.7024	Intermediate Similarity	NPD3618	Phase 1
0.7024	Intermediate Similarity	NPD4138	Approved
0.7024	Intermediate Similarity	NPD6684	Approved
0.7024	Intermediate Similarity	NPD4693	Phase 3
0.7024	Intermediate Similarity	NPD4690	Approved
0.6951	Remote Similarity	NPD3667	Approved
0.6932	Remote Similarity	NPD5133	Approved
0.686	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.686	Remote Similarity	NPD6672	Approved
0.686	Remote Similarity	NPD6903	Approved
0.686	Remote Similarity	NPD4518	Approved
0.686	Remote Similarity	NPD5737	Approved
0.686	Remote Similarity	NPD5208	Approved
0.6818	Remote Similarity	NPD6079	Approved
0.6813	Remote Similarity	NPD3495	Discontinued
0.679	Remote Similarity	NPD4195	Approved
0.6786	Remote Similarity	NPD4786	Approved
0.6786	Remote Similarity	NPD3668	Phase 3
0.6782	Remote Similarity	NPD5328	Approved
0.6782	Remote Similarity	NPD4753	Phase 2
0.6782	Remote Similarity	NPD6673	Approved
0.6782	Remote Similarity	NPD6080	Approved
0.6782	Remote Similarity	NPD6904	Approved
0.6778	Remote Similarity	NPD5654	Approved
0.6707	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.663	Remote Similarity	NPD5959	Approved
0.6629	Remote Similarity	NPD7515	Phase 2
0.6629	Remote Similarity	NPD5693	Phase 1
0.6628	Remote Similarity	NPD6098	Approved
0.6627	Remote Similarity	NPD4692	Approved
0.6627	Remote Similarity	NPD4139	Approved
0.6593	Remote Similarity	NPD4629	Approved
0.6593	Remote Similarity	NPD5210	Approved
0.6593	Remote Similarity	NPD5695	Phase 3
0.6556	Remote Similarity	NPD7631	Approved
0.6556	Remote Similarity	NPD4202	Approved
0.6548	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6533	Remote Similarity	NPD7331	Phase 2
0.6522	Remote Similarity	NPD7732	Phase 3
0.6522	Remote Similarity	NPD7614	Phase 1
0.6522	Remote Similarity	NPD5221	Approved
0.6522	Remote Similarity	NPD5222	Approved
0.6522	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD6404	Discontinued
0.6484	Remote Similarity	NPD7748	Approved
0.6484	Remote Similarity	NPD7900	Approved
0.6484	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD6001	Approved
0.6452	Remote Similarity	NPD5173	Approved
0.6444	Remote Similarity	NPD7609	Phase 3
0.6438	Remote Similarity	NPD4191	Approved
0.6438	Remote Similarity	NPD4192	Approved
0.6438	Remote Similarity	NPD4194	Approved
0.6438	Remote Similarity	NPD4193	Approved
0.6413	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD8262	Approved
0.6344	Remote Similarity	NPD4697	Phase 3
0.6322	Remote Similarity	NPD1694	Approved
0.6316	Remote Similarity	NPD4696	Approved
0.6316	Remote Similarity	NPD5285	Approved
0.6316	Remote Similarity	NPD5286	Approved
0.6279	Remote Similarity	NPD4788	Approved
0.6277	Remote Similarity	NPD6084	Phase 2
0.6277	Remote Similarity	NPD6083	Phase 2
0.6277	Remote Similarity	NPD4755	Approved
0.6277	Remote Similarity	NPD7902	Approved
0.625	Remote Similarity	NPD5223	Approved
0.6211	Remote Similarity	NPD5696	Approved
0.6196	Remote Similarity	NPD6399	Phase 3
0.6186	Remote Similarity	NPD5224	Approved
0.6186	Remote Similarity	NPD5211	Phase 2
0.6186	Remote Similarity	NPD5091	Approved
0.6186	Remote Similarity	NPD5225	Approved
0.6186	Remote Similarity	NPD5226	Approved
0.6186	Remote Similarity	NPD4633	Approved
0.6184	Remote Similarity	NPD7341	Phase 2
0.618	Remote Similarity	NPD650	Approved
0.6146	Remote Similarity	NPD4700	Approved
0.6136	Remote Similarity	NPD1696	Phase 3
0.6125	Remote Similarity	NPD4243	Approved
0.6122	Remote Similarity	NPD5175	Approved
0.6122	Remote Similarity	NPD5174	Approved
0.6098	Remote Similarity	NPD8039	Approved
0.6087	Remote Similarity	NPD6411	Approved
0.6061	Remote Similarity	NPD7812	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD5141	Approved
0.5976	Remote Similarity	NPD4784	Approved
0.5976	Remote Similarity	NPD4785	Approved
0.5972	Remote Similarity	NPD4219	Approved
0.596	Remote Similarity	NPD4754	Approved
0.596	Remote Similarity	NPD6052	Approved
0.5941	Remote Similarity	NPD6614	Approved
0.5941	Remote Similarity	NPD5697	Approved
0.5938	Remote Similarity	NPD1799	Clinical (unspecified phase)
0.5921	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.5904	Remote Similarity	NPD8264	Approved
0.5904	Remote Similarity	NPD6942	Approved
0.5904	Remote Similarity	NPD5275	Approved
0.5904	Remote Similarity	NPD7339	Approved
0.5904	Remote Similarity	NPD4190	Phase 3
0.5897	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD6881	Approved
0.5882	Remote Similarity	NPD4730	Approved
0.5882	Remote Similarity	NPD5128	Approved
0.5882	Remote Similarity	NPD6011	Approved
0.5882	Remote Similarity	NPD6899	Approved
0.5882	Remote Similarity	NPD5168	Approved
0.5882	Remote Similarity	NPD4729	Approved
0.5875	Remote Similarity	NPD6923	Approved
0.5875	Remote Similarity	NPD6922	Approved
0.587	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.587	Remote Similarity	NPD6101	Approved
0.5844	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.5842	Remote Similarity	NPD6402	Approved
0.5842	Remote Similarity	NPD4767	Approved
0.5842	Remote Similarity	NPD6008	Approved
0.5842	Remote Similarity	NPD4768	Approved
0.5842	Remote Similarity	NPD7128	Approved
0.5842	Remote Similarity	NPD6675	Approved
0.5842	Remote Similarity	NPD5739	Approved
0.5833	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD4627	Clinical (unspecified phase)
0.5825	Remote Similarity	NPD6013	Approved
0.5825	Remote Similarity	NPD6012	Approved
0.5825	Remote Similarity	NPD6014	Approved
0.5802	Remote Similarity	NPD7144	Approved
0.5802	Remote Similarity	NPD7143	Approved
0.5795	Remote Similarity	NPD5209	Approved
0.5789	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.5784	Remote Similarity	NPD5701	Approved
0.5784	Remote Similarity	NPD6412	Phase 2
0.5769	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.5769	Remote Similarity	NPD5250	Approved
0.5769	Remote Similarity	NPD5249	Phase 3
0.5769	Remote Similarity	NPD4634	Approved
0.5769	Remote Similarity	NPD5248	Approved
0.5769	Remote Similarity	NPD7102	Approved
0.5769	Remote Similarity	NPD6883	Approved
0.5769	Remote Similarity	NPD7290	Approved
0.5769	Remote Similarity	NPD5169	Approved
0.5769	Remote Similarity	NPD5247	Approved
0.5769	Remote Similarity	NPD5251	Approved
0.5769	Remote Similarity	NPD5135	Approved
0.5755	Remote Similarity	NPD6858	Approved
0.5755	Remote Similarity	NPD7094	Approved
0.5732	Remote Similarity	NPD7152	Approved
0.5732	Remote Similarity	NPD7151	Approved
0.5732	Remote Similarity	NPD7150	Approved
0.5728	Remote Similarity	NPD7320	Approved
0.5727	Remote Similarity	NPD7009	Phase 2
0.5714	Remote Similarity	NPD5127	Approved
0.5714	Remote Similarity	NPD6650	Approved
0.5714	Remote Similarity	NPD6869	Approved
0.5714	Remote Similarity	NPD6847	Approved
0.5714	Remote Similarity	NPD5215	Approved
0.5714	Remote Similarity	NPD5217	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