NPASS Compound

Structure

NPC473230 OpenBabel07101718222D 22 26 0 0 1 0 0 0 0 0999 V2000 -2.7198 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1058 -0.5692 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9269 1.6054 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9269 -1.6054 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8538 -1.0703 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8538 2.1405 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6174 -0.1322 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7446 1.8714 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7358 0.6064 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6608 0.1060 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2955 1.0369 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.9269 0.5351 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.7806 0.5351 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -1.0703 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8538 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.6720 0.2550 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 -2.7806 1.6054 0.0000 C 0 0 2 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 0.8660 -1.5703 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4 7 1 0 0 0 0 4 14 1 0 0 0 0 5 6 1 0 0 0 0 5 16 1 0 0 0 0 6 17 1 0 0 0 0 7 20 1 0 0 0 0 8 12 1 0 0 0 0 8 15 1 0 0 0 0 9 13 1 0 0 0 0 9 20 1 0 0 0 0 10 18 1 0 0 0 0 11 19 1 0 0 0 0 11 21 1 0 0 0 0 12 13 1 0 0 0 0 12 18 1 6 0 0 0 13 18 1 0 0 0 0 14 17 1 6 0 0 0 14 19 1 0 0 0 0 15 17 1 6 0 0 0 15 20 1 0 0 0 0 16 19 1 1 0 0 0 16 22 1 0 0 0 0 17 1 1 6 0 0 0 18 2 1 6 0 0 0 19 3 1 6 0 0 0 20 10 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	304.24
Volume:	329.274
LogP:	3.144
LogD:	2.85
LogS:	0.06
# Rotatable Bonds:	1
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	6
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.777
Synthetic Accessibility Score:	6.201
Fsp3:	1.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.122
MDCK Permeability:	7.384554010059219e-06
Pgp-inhibitor:	0.361
Pgp-substrate:	0.097
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.056
30% Bioavailability (F30%):	0.988

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.339
Plasma Protein Binding (PPB):	68.33910369873047%
Volume Distribution (VD):	0.679
Pgp-substrate:	20.007654190063477%

ADMET: Metabolism

CYP1A2-inhibitor:	0.018
CYP1A2-substrate:	0.434
CYP2C19-inhibitor:	0.011
CYP2C19-substrate:	0.804
CYP2C9-inhibitor:	0.031
CYP2C9-substrate:	0.038
CYP2D6-inhibitor:	0.01
CYP2D6-substrate:	0.177
CYP3A4-inhibitor:	0.947
CYP3A4-substrate:	0.267

ADMET: Excretion

Clearance (CL):	17.721
Half-life (T1/2):	0.267

ADMET: Toxicity

hERG Blockers:	0.066
Human Hepatotoxicity (H-HT):	0.624
Drug-inuced Liver Injury (DILI):	0.038
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.712
Maximum Recommended Daily Dose:	0.84
Skin Sensitization:	0.89
Carcinogencity:	0.904
Eye Corrosion:	0.195
Eye Irritation:	0.026
Respiratory Toxicity:	0.965

Download Data

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

Natural Product: NPC473230

Natural Product ID:	NPC473230
*Common Name:**	PIRXBCDSMORUTK-DEQNQCBWSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	PIRXBCDSMORUTK-DEQNQCBWSA-N
Standard InCHI:	InChI=1S/C20H32O2/c1-17-6-5-16(22)19(3,11-21)14(17)4-7-20-9-13-12(8-15(17)20)18(13,2)10-20/h12-16,21-22H,4-11H2,1-3H3/t12-,13?,14-,15-,16-,17+,18-,19+,20-/m0/s1
SMILES:	CC12CCC(C(C1CCC34C2CC5C(C3)C5(C4)C)(C)CO)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL375896
PubChem CID:	44423990
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0003782] Kaurane 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
NPO12671	Croton zambesicus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17547457]
NPO12671	Croton zambesicus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12671	Croton zambesicus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12671	Croton zambesicus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	2

Activity Type	# Activity
Cell Line	1
Tissue	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	64000.0	nM	PMID[507708]
NPT177	Tissue	Aorta	Rattus norvegicus	IC50	>	80000.0	nM	PMID[507708]

☑ 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 NPC473230 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	409
0.1-0.2	5174
0.2-0.3	18104
0.3-0.4	7893
0.4-0.5	4477
0.5-0.6	4203
0.6-0.7	1840
0.7-0.8	464
0.8-0.85	91
0.85-0.9	26
0.9-0.95	11
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC475884
0.9677	High Similarity	NPC473276
0.9677	High Similarity	NPC41577
0.9677	High Similarity	NPC474380
0.9516	High Similarity	NPC69149
0.9385	High Similarity	NPC470830
0.9385	High Similarity	NPC299948
0.9385	High Similarity	NPC241085
0.9355	High Similarity	NPC114891
0.9219	High Similarity	NPC142712
0.9194	High Similarity	NPC218585
0.9194	High Similarity	NPC71460
0.9194	High Similarity	NPC148174
0.9118	High Similarity	NPC478130
0.9104	High Similarity	NPC195530
0.9104	High Similarity	NPC473279
0.9091	High Similarity	NPC107919
0.9077	High Similarity	NPC48079
0.8971	High Similarity	NPC473238
0.8971	High Similarity	NPC472341
0.8939	High Similarity	NPC472741
0.8923	High Similarity	NPC44122
0.8906	High Similarity	NPC118937
0.8906	High Similarity	NPC281540
0.8906	High Similarity	NPC167995
0.8906	High Similarity	NPC159654
0.8889	High Similarity	NPC95804
0.8889	High Similarity	NPC185547
0.8806	High Similarity	NPC129829
0.8806	High Similarity	NPC477820
0.8806	High Similarity	NPC66407
0.8806	High Similarity	NPC254037
0.8714	High Similarity	NPC273366
0.8714	High Similarity	NPC70982
0.8714	High Similarity	NPC230704
0.871	High Similarity	NPC476735
0.8676	High Similarity	NPC231945
0.8676	High Similarity	NPC63588
0.8676	High Similarity	NPC251201
0.8676	High Similarity	NPC232925
0.8676	High Similarity	NPC192192
0.8676	High Similarity	NPC282454
0.8611	High Similarity	NPC147993
0.8611	High Similarity	NPC471769
0.8592	High Similarity	NPC470145
0.8571	High Similarity	NPC10476
0.8571	High Similarity	NPC254509
0.8571	High Similarity	NPC95958
0.8571	High Similarity	NPC228994
0.8571	High Similarity	NPC196358
0.8571	High Similarity	NPC49168
0.8571	High Similarity	NPC192501
0.8571	High Similarity	NPC145552
0.8571	High Similarity	NPC5046
0.8571	High Similarity	NPC304499
0.8551	High Similarity	NPC470071
0.8551	High Similarity	NPC1340
0.8551	High Similarity	NPC478103
0.8551	High Similarity	NPC127094
0.8551	High Similarity	NPC100586
0.8551	High Similarity	NPC252182
0.8551	High Similarity	NPC187471
0.8551	High Similarity	NPC157422
0.8551	High Similarity	NPC109457
0.8507	High Similarity	NPC63190
0.8493	Intermediate Similarity	NPC287452
0.8472	Intermediate Similarity	NPC257191
0.8472	Intermediate Similarity	NPC331618
0.8472	Intermediate Similarity	NPC475031
0.8472	Intermediate Similarity	NPC476233
0.8451	Intermediate Similarity	NPC243027
0.8451	Intermediate Similarity	NPC200243
0.8451	Intermediate Similarity	NPC317242
0.8451	Intermediate Similarity	NPC196136
0.8451	Intermediate Similarity	NPC158208
0.8429	Intermediate Similarity	NPC232112
0.8429	Intermediate Similarity	NPC153719
0.8429	Intermediate Similarity	NPC470610
0.8429	Intermediate Similarity	NPC195489
0.8382	Intermediate Similarity	NPC474756
0.8356	Intermediate Similarity	NPC472342
0.8333	Intermediate Similarity	NPC78067
0.8333	Intermediate Similarity	NPC278091
0.8333	Intermediate Similarity	NPC93662
0.8333	Intermediate Similarity	NPC163597
0.831	Intermediate Similarity	NPC48795
0.831	Intermediate Similarity	NPC477508
0.8286	Intermediate Similarity	NPC157777
0.8286	Intermediate Similarity	NPC8004
0.8286	Intermediate Similarity	NPC127283
0.8286	Intermediate Similarity	NPC320549
0.8286	Intermediate Similarity	NPC131506
0.8286	Intermediate Similarity	NPC156277
0.8286	Intermediate Similarity	NPC111234
0.8286	Intermediate Similarity	NPC58057
0.8286	Intermediate Similarity	NPC151018
0.8261	Intermediate Similarity	NPC99264
0.8254	Intermediate Similarity	NPC135438
0.8219	Intermediate Similarity	NPC477227
0.8219	Intermediate Similarity	NPC185915
0.8219	Intermediate Similarity	NPC302578
0.8219	Intermediate Similarity	NPC192046
0.8219	Intermediate Similarity	NPC133596
0.8219	Intermediate Similarity	NPC128951
0.8219	Intermediate Similarity	NPC11907
0.8219	Intermediate Similarity	NPC105208
0.8209	Intermediate Similarity	NPC243469
0.8209	Intermediate Similarity	NPC260116
0.8209	Intermediate Similarity	NPC80463
0.8209	Intermediate Similarity	NPC475943
0.8209	Intermediate Similarity	NPC190827
0.8209	Intermediate Similarity	NPC472946
0.8194	Intermediate Similarity	NPC212879
0.8194	Intermediate Similarity	NPC240235
0.8194	Intermediate Similarity	NPC185536
0.8194	Intermediate Similarity	NPC231680
0.8194	Intermediate Similarity	NPC178383
0.8194	Intermediate Similarity	NPC212733
0.8194	Intermediate Similarity	NPC91387
0.8194	Intermediate Similarity	NPC270306
0.8194	Intermediate Similarity	NPC3403
0.8194	Intermediate Similarity	NPC104387
0.8194	Intermediate Similarity	NPC231256
0.8194	Intermediate Similarity	NPC97534
0.8194	Intermediate Similarity	NPC174964
0.8194	Intermediate Similarity	NPC195155
0.8182	Intermediate Similarity	NPC249078
0.8182	Intermediate Similarity	NPC292419
0.8182	Intermediate Similarity	NPC290791
0.8182	Intermediate Similarity	NPC236099
0.8182	Intermediate Similarity	NPC209686
0.8158	Intermediate Similarity	NPC475388
0.8143	Intermediate Similarity	NPC45296
0.8133	Intermediate Similarity	NPC16449
0.8116	Intermediate Similarity	NPC469987
0.8108	Intermediate Similarity	NPC67657
0.8108	Intermediate Similarity	NPC18857
0.8108	Intermediate Similarity	NPC65897
0.8108	Intermediate Similarity	NPC302041
0.8108	Intermediate Similarity	NPC31828
0.8108	Intermediate Similarity	NPC85346
0.8082	Intermediate Similarity	NPC477602
0.8082	Intermediate Similarity	NPC472486
0.8082	Intermediate Similarity	NPC477601
0.8082	Intermediate Similarity	NPC91573
0.8082	Intermediate Similarity	NPC5767
0.8082	Intermediate Similarity	NPC14112
0.8082	Intermediate Similarity	NPC472487
0.8082	Intermediate Similarity	NPC4209
0.8082	Intermediate Similarity	NPC473916
0.8082	Intermediate Similarity	NPC475742
0.8082	Intermediate Similarity	NPC86305
0.8056	Intermediate Similarity	NPC472503
0.8056	Intermediate Similarity	NPC192638
0.8056	Intermediate Similarity	NPC308440
0.8056	Intermediate Similarity	NPC254340
0.8056	Intermediate Similarity	NPC167702
0.8056	Intermediate Similarity	NPC62657
0.8056	Intermediate Similarity	NPC25511
0.8056	Intermediate Similarity	NPC280026
0.8052	Intermediate Similarity	NPC113978
0.8028	Intermediate Similarity	NPC89310
0.8026	Intermediate Similarity	NPC12933
0.8026	Intermediate Similarity	NPC469745
0.8	Intermediate Similarity	NPC213178
0.8	Intermediate Similarity	NPC475727
0.8	Intermediate Similarity	NPC472742
0.8	Intermediate Similarity	NPC327728
0.8	Intermediate Similarity	NPC6120
0.8	Intermediate Similarity	NPC80297
0.8	Intermediate Similarity	NPC81074
0.8	Intermediate Similarity	NPC477282
0.8	Intermediate Similarity	NPC269333
0.8	Intermediate Similarity	NPC131892
0.8	Intermediate Similarity	NPC116119
0.8	Intermediate Similarity	NPC470833
0.7973	Intermediate Similarity	NPC212241
0.7973	Intermediate Similarity	NPC317913
0.7973	Intermediate Similarity	NPC260301
0.7973	Intermediate Similarity	NPC119355
0.7973	Intermediate Similarity	NPC143133
0.7973	Intermediate Similarity	NPC298168
0.7973	Intermediate Similarity	NPC474574
0.7973	Intermediate Similarity	NPC264602
0.7973	Intermediate Similarity	NPC221420
0.7973	Intermediate Similarity	NPC23884
0.7973	Intermediate Similarity	NPC307336
0.7973	Intermediate Similarity	NPC248830
0.7973	Intermediate Similarity	NPC64081
0.7973	Intermediate Similarity	NPC207010
0.7973	Intermediate Similarity	NPC202540
0.7971	Intermediate Similarity	NPC204233
0.7969	Intermediate Similarity	NPC236588
0.7945	Intermediate Similarity	NPC186851
0.7945	Intermediate Similarity	NPC21220
0.7945	Intermediate Similarity	NPC125767
0.7945	Intermediate Similarity	NPC103822
0.7941	Intermediate Similarity	NPC477603
0.7917	Intermediate Similarity	NPC253805
0.7895	Intermediate Similarity	NPC475679

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 NPC473230 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	415
0.1-0.2	4606
0.2-0.3	3019
0.3-0.4	654
0.4-0.5	180
0.5-0.6	213
0.6-0.7	39
0.7-0.8	23
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
0.9091	High Similarity	NPD4267	Clinical (unspecified phase)
0.8406	Intermediate Similarity	NPD4787	Phase 1
0.8286	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.8286	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.8082	Intermediate Similarity	NPD6117	Approved
0.8056	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7973	Intermediate Similarity	NPD6116	Phase 1
0.7867	Intermediate Similarity	NPD6697	Approved
0.7867	Intermediate Similarity	NPD6115	Approved
0.7867	Intermediate Similarity	NPD6114	Approved
0.7867	Intermediate Similarity	NPD6118	Approved
0.7703	Intermediate Similarity	NPD3703	Phase 2
0.7662	Intermediate Similarity	NPD7525	Registered
0.7639	Intermediate Similarity	NPD4244	Approved
0.7639	Intermediate Similarity	NPD4789	Approved
0.7639	Intermediate Similarity	NPD4245	Approved
0.7606	Intermediate Similarity	NPD5360	Phase 3
0.7606	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3698	Phase 2
0.7436	Intermediate Similarity	NPD6928	Phase 2
0.7429	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD6942	Approved
0.7237	Intermediate Similarity	NPD7339	Approved
0.7195	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD3671	Phase 1
0.7123	Intermediate Similarity	NPD6705	Phase 1
0.7089	Intermediate Similarity	NPD7645	Phase 2
0.7067	Intermediate Similarity	NPD4758	Discontinued
0.6935	Remote Similarity	NPD385	Approved
0.6935	Remote Similarity	NPD384	Approved
0.6923	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD4224	Phase 2
0.6842	Remote Similarity	NPD6081	Approved
0.679	Remote Similarity	NPD4748	Discontinued
0.6782	Remote Similarity	NPD6701	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD6700	Approved
0.675	Remote Similarity	NPD5364	Discontinued
0.6705	Remote Similarity	NPD6702	Approved
0.6705	Remote Similarity	NPD6703	Approved
0.6667	Remote Similarity	NPD6924	Approved
0.6667	Remote Similarity	NPD6926	Approved
0.6667	Remote Similarity	NPD4786	Approved
0.6667	Remote Similarity	NPD5328	Approved
0.6629	Remote Similarity	NPD8171	Discontinued
0.6623	Remote Similarity	NPD5777	Approved
0.6582	Remote Similarity	NPD3702	Approved
0.6548	Remote Similarity	NPD4788	Approved
0.6517	Remote Similarity	NPD8035	Phase 2
0.6517	Remote Similarity	NPD6079	Approved
0.6517	Remote Similarity	NPD8034	Phase 2
0.6512	Remote Similarity	NPD3618	Phase 1
0.65	Remote Similarity	NPD6933	Approved
0.6463	Remote Similarity	NPD6929	Approved
0.6429	Remote Similarity	NPD3667	Approved
0.641	Remote Similarity	NPD4243	Approved
0.641	Remote Similarity	NPD7150	Approved
0.641	Remote Similarity	NPD7151	Approved
0.641	Remote Similarity	NPD7152	Approved
0.6386	Remote Similarity	NPD6930	Phase 2
0.6386	Remote Similarity	NPD6931	Approved
0.6364	Remote Similarity	NPD6923	Approved
0.6364	Remote Similarity	NPD6922	Approved
0.6351	Remote Similarity	NPD371	Approved
0.6344	Remote Similarity	NPD7919	Phase 3
0.6344	Remote Similarity	NPD7920	Phase 3
0.6322	Remote Similarity	NPD8308	Discontinued
0.631	Remote Similarity	NPD6902	Approved
0.6282	Remote Similarity	NPD7143	Approved
0.6282	Remote Similarity	NPD7144	Approved
0.6277	Remote Similarity	NPD8088	Phase 1
0.6264	Remote Similarity	NPD4202	Approved
0.625	Remote Similarity	NPD4785	Approved
0.625	Remote Similarity	NPD4784	Approved
0.625	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.622	Remote Similarity	NPD6925	Approved
0.622	Remote Similarity	NPD5776	Phase 2
0.622	Remote Similarity	NPD6932	Approved
0.6211	Remote Similarity	NPD8418	Phase 2
0.619	Remote Similarity	NPD7509	Discontinued
0.617	Remote Similarity	NPD4755	Approved
0.6163	Remote Similarity	NPD6695	Phase 3
0.6145	Remote Similarity	NPD7145	Approved
0.6129	Remote Similarity	NPD7991	Discontinued
0.6105	Remote Similarity	NPD7638	Approved
0.6092	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6092	Remote Similarity	NPD3666	Approved
0.6092	Remote Similarity	NPD3133	Approved
0.6092	Remote Similarity	NPD3665	Phase 1
0.6071	Remote Similarity	NPD6683	Phase 2
0.6064	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6064	Remote Similarity	NPD5221	Approved
0.6064	Remote Similarity	NPD5222	Approved
0.6064	Remote Similarity	NPD4697	Phase 3
0.6042	Remote Similarity	NPD4700	Approved
0.6042	Remote Similarity	NPD5285	Approved
0.6042	Remote Similarity	NPD4696	Approved
0.6042	Remote Similarity	NPD7640	Approved
0.6042	Remote Similarity	NPD7639	Approved
0.6042	Remote Similarity	NPD5286	Approved
0.6023	Remote Similarity	NPD6893	Approved
0.6	Remote Similarity	NPD388	Approved
0.6	Remote Similarity	NPD5173	Approved
0.6	Remote Similarity	NPD386	Approved
0.6	Remote Similarity	NPD7514	Phase 3
0.5979	Remote Similarity	NPD4159	Approved
0.5978	Remote Similarity	NPD7515	Phase 2
0.5976	Remote Similarity	NPD5275	Approved
0.5976	Remote Similarity	NPD4190	Phase 3
0.596	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.5934	Remote Similarity	NPD4753	Phase 2
0.5918	Remote Similarity	NPD5226	Approved
0.5918	Remote Similarity	NPD4633	Approved
0.5918	Remote Similarity	NPD5224	Approved
0.5918	Remote Similarity	NPD5211	Phase 2
0.5918	Remote Similarity	NPD7632	Discontinued
0.5918	Remote Similarity	NPD5225	Approved
0.5914	Remote Similarity	NPD6399	Phase 3
0.59	Remote Similarity	NPD7128	Approved
0.59	Remote Similarity	NPD5739	Approved
0.59	Remote Similarity	NPD6402	Approved
0.59	Remote Similarity	NPD6675	Approved
0.5889	Remote Similarity	NPD7750	Discontinued
0.5889	Remote Similarity	NPD7524	Approved
0.5882	Remote Similarity	NPD4195	Approved
0.5859	Remote Similarity	NPD5175	Approved
0.5859	Remote Similarity	NPD5174	Approved
0.5816	Remote Similarity	NPD5223	Approved
0.5814	Remote Similarity	NPD7332	Phase 2
0.5811	Remote Similarity	NPD3198	Approved
0.58	Remote Similarity	NPD5141	Approved
0.5784	Remote Similarity	NPD7320	Approved
0.5784	Remote Similarity	NPD6881	Approved
0.5784	Remote Similarity	NPD6899	Approved
0.5778	Remote Similarity	NPD5279	Phase 3
0.5773	Remote Similarity	NPD5290	Discontinued
0.5765	Remote Similarity	NPD3617	Approved
0.5765	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.5747	Remote Similarity	NPD6898	Phase 1
0.5743	Remote Similarity	NPD4767	Approved
0.5743	Remote Similarity	NPD4768	Approved
0.5743	Remote Similarity	NPD6920	Discontinued
0.573	Remote Similarity	NPD3668	Phase 3
0.5728	Remote Similarity	NPD6372	Approved
0.5728	Remote Similarity	NPD6373	Approved
0.57	Remote Similarity	NPD4754	Approved
0.5686	Remote Similarity	NPD5701	Approved
0.5686	Remote Similarity	NPD5697	Approved
0.5684	Remote Similarity	NPD7748	Approved
0.5682	Remote Similarity	NPD4223	Phase 3
0.5682	Remote Similarity	NPD4221	Approved
0.5673	Remote Similarity	NPD6883	Approved
0.5673	Remote Similarity	NPD7102	Approved
0.5673	Remote Similarity	NPD7290	Approved
0.567	Remote Similarity	NPD6084	Phase 2
0.567	Remote Similarity	NPD6083	Phase 2
0.5667	Remote Similarity	NPD5329	Approved
0.5663	Remote Similarity	NPD1811	Approved
0.5663	Remote Similarity	NPD1810	Approved
0.5638	Remote Similarity	NPD7087	Discontinued
0.5631	Remote Similarity	NPD4729	Approved
0.5631	Remote Similarity	NPD5128	Approved
0.5631	Remote Similarity	NPD6415	Discontinued
0.5631	Remote Similarity	NPD4730	Approved
0.5625	Remote Similarity	NPD4629	Approved
0.5625	Remote Similarity	NPD5210	Approved
0.5619	Remote Similarity	NPD8130	Phase 1
0.5619	Remote Similarity	NPD6650	Approved
0.5619	Remote Similarity	NPD6869	Approved
0.5619	Remote Similarity	NPD6847	Approved
0.5619	Remote Similarity	NPD6617	Approved
0.5619	Remote Similarity	NPD6649	Approved
0.5616	Remote Similarity	NPD586	Phase 1
0.5604	Remote Similarity	NPD3574	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