NPASS Compound

Structure

CID290367 OpenBabel06191716102D 31 31 0 0 1 0 0 0 0 0999 V2000 12.9904 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.8564 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 C 0 0 0 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 0.5000 0.8660 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 6.0622 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.2583 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.1244 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3923 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 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 12.9904 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -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 0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 23 1 0 0 0 0 2 23 1 0 0 0 0 3 24 1 0 0 0 0 4 25 1 0 0 0 0 5 26 1 0 0 0 0 6 27 1 0 0 0 0 7 30 1 0 0 0 0 8 30 1 0 0 0 0 9 10 1 0 0 0 0 9 14 1 0 0 0 0 10 15 1 0 0 0 0 11 13 1 0 0 0 0 11 16 1 0 0 0 0 12 17 1 0 0 0 0 12 18 1 0 0 0 0 13 23 2 0 0 0 0 14 24 2 0 0 0 0 15 26 2 0 0 0 0 16 25 1 0 0 0 0 17 24 1 0 0 0 0 18 25 2 0 0 0 0 19 21 1 0 0 0 0 19 26 1 0 0 0 0 20 22 1 0 0 0 0 20 27 2 0 0 0 0 22 29 1 0 0 0 0 27 28 1 0 0 0 0 28 21 1 6 0 0 0 28 30 1 0 0 0 0 29 30 1 0 0 0 0 29 31 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	426.39
Volume:	514.487
LogP:	8.942
LogD:	6.323
LogS:	-6.091
# Rotatable Bonds:	12
TPSA:	20.23
# H-Bond Aceptor:	1
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.243
Synthetic Accessibility Score:	4.137
Fsp3:	0.667
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.766
MDCK Permeability:	1.3535966900235508e-05
Pgp-inhibitor:	0.027
Pgp-substrate:	0.201
Human Intestinal Absorption (HIA):	0.185
20% Bioavailability (F20%):	0.992
30% Bioavailability (F30%):	0.993

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.269
Plasma Protein Binding (PPB):	95.68009948730469%
Volume Distribution (VD):	2.777
Pgp-substrate:	3.3208374977111816%

ADMET: Metabolism

CYP1A2-inhibitor:	0.103
CYP1A2-substrate:	0.168
CYP2C19-inhibitor:	0.218
CYP2C19-substrate:	0.075
CYP2C9-inhibitor:	0.284
CYP2C9-substrate:	0.974
CYP2D6-inhibitor:	0.223
CYP2D6-substrate:	0.398
CYP3A4-inhibitor:	0.528
CYP3A4-substrate:	0.167

ADMET: Excretion

Clearance (CL):	4.95
Half-life (T1/2):	0.042

ADMET: Toxicity

hERG Blockers:	0.013
Human Hepatotoxicity (H-HT):	0.456
Drug-inuced Liver Injury (DILI):	0.002
AMES Toxicity:	0.0
Rat Oral Acute Toxicity:	0.003
Maximum Recommended Daily Dose:	0.989
Skin Sensitization:	0.963
Carcinogencity:	0.01
Eye Corrosion:	0.223
Eye Irritation:	0.698
Respiratory Toxicity:	0.047

Download Data

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

Natural Product: NPC290367

Natural Product ID:	NPC290367
*Common Name:**	Camelliol C
IUPAC Name:	(1S,5R)-4,6,6-trimethyl-5-[(3E,7E,11E)-3,8,12,16-tetramethylheptadeca-3,7,11,15-tetraenyl]cyclohex-3-en-1-ol
Synonyms:	Camelliol C
Standard InCHIKey:	CIDHBCQEXDUWEB-HJSIMFEZSA-N
Standard InCHI:	InChI=1S/C30H50O/c1-23(2)13-11-16-25(4)18-12-17-24(3)14-9-10-15-26(5)19-21-28-27(6)20-22-29(31)30(28,7)8/h13-15,18,20,28-29,31H,9-12,16-17,19,21-22H2,1-8H3/b24-14+,25-18+,26-15+/t28-,29+/m1/s1
SMILES:	C/C(=CCC/C=C(/CC[C@@H]1C(=CC[C@@H](C1(C)C)O)C)C)/CC/C=C(/CCC=C(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL463552
PubChem CID:	6476390
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO10031	Euphorbia antiquorum	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11858748]
NPO25515	Garcinia speciosa	Species	Clusiaceae	Eukaryota	barks	n.a.	n.a.	PMID[15620248]
NPO10031	Euphorbia antiquorum	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24840014]
NPO10031	Euphorbia antiquorum	Species	Euphorbiaceae	Eukaryota	Stems	n.a.	n.a.	PMID[31180680]
NPO10031	Euphorbia antiquorum	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25515	Garcinia speciosa	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10031	Euphorbia antiquorum	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25515	Garcinia speciosa	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10031	Euphorbia antiquorum	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25515	Garcinia speciosa	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
Others	5

Activity Type	# Activity
Cell Line	1
Others	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT80	Cell Line	Raji	Homo sapiens	Activity	=	70.0	%	PMID[496408]
NPT2	Others	Unspecified		Activity	=	20.1	%	PMID[496408]
NPT2	Others	Unspecified		Activity	=	51.5	%	PMID[496408]
NPT2	Others	Unspecified		Activity	=	86.3	%	PMID[496408]
NPT2	Others	Unspecified		Activity	=	100.0	%	PMID[496408]

☑ 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 NPC290367 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	161
0.1-0.2	1909
0.2-0.3	11617
0.3-0.4	14158
0.4-0.5	7782
0.5-0.6	5344
0.6-0.7	1386
0.7-0.8	304
0.8-0.85	29
0.85-0.9	5
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9365	High Similarity	NPC208999
0.9206	High Similarity	NPC114651
0.8806	High Similarity	NPC471799
0.8788	High Similarity	NPC145498
0.873	High Similarity	NPC225415
0.871	High Similarity	NPC475251
0.8676	High Similarity	NPC243342
0.8676	High Similarity	NPC471797
0.8676	High Similarity	NPC477138
0.8657	High Similarity	NPC242001
0.8551	High Similarity	NPC288035
0.8551	High Similarity	NPC66566
0.8551	High Similarity	NPC285893
0.8551	High Similarity	NPC28657
0.8551	High Similarity	NPC162742
0.8551	High Similarity	NPC304309
0.8551	High Similarity	NPC136188
0.8551	High Similarity	NPC291503
0.8551	High Similarity	NPC134847
0.8551	High Similarity	NPC22105
0.8551	High Similarity	NPC477923
0.8551	High Similarity	NPC230301
0.8529	High Similarity	NPC182717
0.8507	High Similarity	NPC34834
0.8507	High Similarity	NPC92801
0.8462	Intermediate Similarity	NPC476039
0.8462	Intermediate Similarity	NPC286669
0.8462	Intermediate Similarity	NPC222366
0.8429	Intermediate Similarity	NPC107059
0.8429	Intermediate Similarity	NPC240604
0.8429	Intermediate Similarity	NPC113733
0.8429	Intermediate Similarity	NPC274079
0.8429	Intermediate Similarity	NPC106364
0.8429	Intermediate Similarity	NPC477925
0.8429	Intermediate Similarity	NPC265588
0.8429	Intermediate Similarity	NPC321016
0.8429	Intermediate Similarity	NPC300324
0.8429	Intermediate Similarity	NPC321381
0.8406	Intermediate Similarity	NPC91858
0.8406	Intermediate Similarity	NPC100334
0.8382	Intermediate Similarity	NPC110799
0.8382	Intermediate Similarity	NPC167706
0.8333	Intermediate Similarity	NPC197805
0.8333	Intermediate Similarity	NPC96962
0.831	Intermediate Similarity	NPC318495
0.831	Intermediate Similarity	NPC34019
0.831	Intermediate Similarity	NPC198968
0.831	Intermediate Similarity	NPC155986
0.831	Intermediate Similarity	NPC477924
0.831	Intermediate Similarity	NPC471798
0.8308	Intermediate Similarity	NPC163678
0.8286	Intermediate Similarity	NPC313179
0.8286	Intermediate Similarity	NPC141071
0.8286	Intermediate Similarity	NPC69383
0.8286	Intermediate Similarity	NPC257347
0.8286	Intermediate Similarity	NPC471723
0.8286	Intermediate Similarity	NPC171148
0.8261	Intermediate Similarity	NPC68443
0.8261	Intermediate Similarity	NPC474140
0.8209	Intermediate Similarity	NPC96484
0.8209	Intermediate Similarity	NPC216460
0.8194	Intermediate Similarity	NPC99168
0.8194	Intermediate Similarity	NPC83351
0.8194	Intermediate Similarity	NPC22955
0.8194	Intermediate Similarity	NPC307965
0.8194	Intermediate Similarity	NPC167891
0.8194	Intermediate Similarity	NPC18603
0.8194	Intermediate Similarity	NPC477522
0.8194	Intermediate Similarity	NPC473943
0.8194	Intermediate Similarity	NPC470396
0.8194	Intermediate Similarity	NPC474216
0.8194	Intermediate Similarity	NPC76931
0.8194	Intermediate Similarity	NPC474989
0.8194	Intermediate Similarity	NPC275910
0.8194	Intermediate Similarity	NPC87604
0.8194	Intermediate Similarity	NPC476314
0.8182	Intermediate Similarity	NPC202017
0.8182	Intermediate Similarity	NPC250977
0.8182	Intermediate Similarity	NPC149680
0.8169	Intermediate Similarity	NPC470362
0.8169	Intermediate Similarity	NPC46160
0.8169	Intermediate Similarity	NPC27765
0.8169	Intermediate Similarity	NPC290598
0.8169	Intermediate Similarity	NPC96319
0.8169	Intermediate Similarity	NPC30590
0.8169	Intermediate Similarity	NPC120098
0.8169	Intermediate Similarity	NPC122418
0.8169	Intermediate Similarity	NPC265328
0.8169	Intermediate Similarity	NPC134330
0.8169	Intermediate Similarity	NPC189883
0.8169	Intermediate Similarity	NPC202642
0.8169	Intermediate Similarity	NPC129165
0.8154	Intermediate Similarity	NPC309300
0.8143	Intermediate Similarity	NPC469534
0.8143	Intermediate Similarity	NPC469533
0.8143	Intermediate Similarity	NPC469593
0.8143	Intermediate Similarity	NPC306727
0.8116	Intermediate Similarity	NPC164022
0.8116	Intermediate Similarity	NPC477792
0.8095	Intermediate Similarity	NPC122239
0.8088	Intermediate Similarity	NPC471560
0.8088	Intermediate Similarity	NPC269877
0.8088	Intermediate Similarity	NPC167272
0.8088	Intermediate Similarity	NPC473893
0.8088	Intermediate Similarity	NPC474248
0.8082	Intermediate Similarity	NPC109546
0.8082	Intermediate Similarity	NPC28862
0.8082	Intermediate Similarity	NPC84694
0.8082	Intermediate Similarity	NPC143182
0.8082	Intermediate Similarity	NPC47982
0.8082	Intermediate Similarity	NPC81306
0.8082	Intermediate Similarity	NPC53744
0.8082	Intermediate Similarity	NPC291379
0.8082	Intermediate Similarity	NPC328714
0.806	Intermediate Similarity	NPC69649
0.806	Intermediate Similarity	NPC45782
0.806	Intermediate Similarity	NPC68703
0.8056	Intermediate Similarity	NPC214570
0.8056	Intermediate Similarity	NPC40394
0.8056	Intermediate Similarity	NPC472805
0.8056	Intermediate Similarity	NPC101475
0.8056	Intermediate Similarity	NPC90979
0.8056	Intermediate Similarity	NPC91594
0.8056	Intermediate Similarity	NPC34177
0.8056	Intermediate Similarity	NPC283619
0.8056	Intermediate Similarity	NPC157996
0.803	Intermediate Similarity	NPC238352
0.803	Intermediate Similarity	NPC477009
0.8028	Intermediate Similarity	NPC118508
0.8028	Intermediate Similarity	NPC322353
0.8028	Intermediate Similarity	NPC34700
0.8028	Intermediate Similarity	NPC138374
0.8028	Intermediate Similarity	NPC121744
0.8	Intermediate Similarity	NPC279200
0.7973	Intermediate Similarity	NPC241290
0.7973	Intermediate Similarity	NPC209944
0.7973	Intermediate Similarity	NPC26117
0.7973	Intermediate Similarity	NPC234193
0.7973	Intermediate Similarity	NPC96362
0.7973	Intermediate Similarity	NPC287749
0.7973	Intermediate Similarity	NPC164840
0.7971	Intermediate Similarity	NPC49422
0.7971	Intermediate Similarity	NPC9161
0.7969	Intermediate Similarity	NPC135648
0.7945	Intermediate Similarity	NPC300499
0.7945	Intermediate Similarity	NPC158662
0.7945	Intermediate Similarity	NPC230295
0.7945	Intermediate Similarity	NPC318136
0.7945	Intermediate Similarity	NPC205455
0.7945	Intermediate Similarity	NPC196753
0.7945	Intermediate Similarity	NPC186191
0.7945	Intermediate Similarity	NPC98386
0.7945	Intermediate Similarity	NPC253807
0.7941	Intermediate Similarity	NPC32055
0.7941	Intermediate Similarity	NPC160209
0.7941	Intermediate Similarity	NPC471238
0.7917	Intermediate Similarity	NPC167873
0.7917	Intermediate Similarity	NPC1973
0.7917	Intermediate Similarity	NPC253190
0.7917	Intermediate Similarity	NPC237460
0.7917	Intermediate Similarity	NPC247325
0.7917	Intermediate Similarity	NPC106432
0.7917	Intermediate Similarity	NPC73875
0.7917	Intermediate Similarity	NPC244488
0.791	Intermediate Similarity	NPC279434
0.7903	Intermediate Similarity	NPC48891
0.7887	Intermediate Similarity	NPC329090
0.7887	Intermediate Similarity	NPC476366
0.7887	Intermediate Similarity	NPC201048
0.7887	Intermediate Similarity	NPC27395
0.7879	Intermediate Similarity	NPC323424
0.7879	Intermediate Similarity	NPC144650
0.7879	Intermediate Similarity	NPC96793
0.7879	Intermediate Similarity	NPC107540
0.7867	Intermediate Similarity	NPC7505
0.7867	Intermediate Similarity	NPC82986
0.7867	Intermediate Similarity	NPC470383
0.7867	Intermediate Similarity	NPC474731
0.7867	Intermediate Similarity	NPC474752
0.7867	Intermediate Similarity	NPC209620
0.7867	Intermediate Similarity	NPC474759
0.7867	Intermediate Similarity	NPC474683
0.7867	Intermediate Similarity	NPC23852
0.7867	Intermediate Similarity	NPC47761
0.7867	Intermediate Similarity	NPC264245
0.7867	Intermediate Similarity	NPC476646
0.7867	Intermediate Similarity	NPC142163
0.7867	Intermediate Similarity	NPC474531
0.7857	Intermediate Similarity	NPC242992
0.7846	Intermediate Similarity	NPC274704
0.7838	Intermediate Similarity	NPC472463
0.7838	Intermediate Similarity	NPC1319
0.7838	Intermediate Similarity	NPC209430
0.7838	Intermediate Similarity	NPC30986
0.7838	Intermediate Similarity	NPC100906
0.7826	Intermediate Similarity	NPC9942
0.7808	Intermediate Similarity	NPC470758
0.7808	Intermediate Similarity	NPC470711
0.7808	Intermediate Similarity	NPC130136
0.7794	Intermediate Similarity	NPC171225

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 NPC290367 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	163
0.1-0.2	2528
0.2-0.3	4010
0.3-0.4	1751
0.4-0.5	436
0.5-0.6	187
0.6-0.7	59
0.7-0.8	15
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
0.8551	High Similarity	NPD6942	Approved
0.8551	High Similarity	NPD7339	Approved
0.8286	Intermediate Similarity	NPD8264	Approved
0.8169	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.8116	Intermediate Similarity	NPD7151	Approved
0.8116	Intermediate Similarity	NPD7150	Approved
0.8116	Intermediate Similarity	NPD7152	Approved
0.8088	Intermediate Similarity	NPD6922	Approved
0.8088	Intermediate Similarity	NPD6923	Approved
0.7971	Intermediate Similarity	NPD7144	Approved
0.7971	Intermediate Similarity	NPD7143	Approved
0.7887	Intermediate Similarity	NPD6924	Approved
0.7887	Intermediate Similarity	NPD6926	Approved
0.7838	Intermediate Similarity	NPD7645	Phase 2
0.7671	Intermediate Similarity	NPD6933	Approved
0.7564	Intermediate Similarity	NPD4786	Approved
0.7532	Intermediate Similarity	NPD3667	Approved
0.75	Intermediate Similarity	NPD7525	Registered
0.7397	Intermediate Similarity	NPD4784	Approved
0.7397	Intermediate Similarity	NPD4785	Approved
0.7368	Intermediate Similarity	NPD6929	Approved
0.7361	Intermediate Similarity	NPD4243	Approved
0.7333	Intermediate Similarity	NPD6925	Approved
0.7333	Intermediate Similarity	NPD5776	Phase 2
0.7333	Intermediate Similarity	NPD6932	Approved
0.7313	Intermediate Similarity	NPD368	Approved
0.7273	Intermediate Similarity	NPD6931	Approved
0.7273	Intermediate Similarity	NPD6930	Phase 2
0.7273	Intermediate Similarity	NPD7509	Discontinued
0.7237	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD7145	Approved
0.7188	Intermediate Similarity	NPD342	Phase 1
0.7143	Intermediate Similarity	NPD6683	Phase 2
0.7077	Intermediate Similarity	NPD4219	Approved
0.7073	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD4748	Discontinued
0.7051	Intermediate Similarity	NPD7514	Phase 3
0.7051	Intermediate Similarity	NPD7332	Phase 2
0.7	Intermediate Similarity	NPD6695	Phase 3
0.6962	Remote Similarity	NPD6902	Approved
0.6962	Remote Similarity	NPD6898	Phase 1
0.6951	Remote Similarity	NPD3618	Phase 1
0.6914	Remote Similarity	NPD3665	Phase 1
0.6914	Remote Similarity	NPD3133	Approved
0.6914	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD3666	Approved
0.6905	Remote Similarity	NPD5328	Approved
0.6842	Remote Similarity	NPD5275	Approved
0.6842	Remote Similarity	NPD4190	Phase 3
0.6835	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD6893	Approved
0.6747	Remote Similarity	NPD5279	Phase 3
0.6744	Remote Similarity	NPD7515	Phase 2
0.6744	Remote Similarity	NPD6079	Approved
0.6707	Remote Similarity	NPD3668	Phase 3
0.6667	Remote Similarity	NPD7750	Discontinued
0.6667	Remote Similarity	NPD6399	Phase 3
0.6667	Remote Similarity	NPD7524	Approved
0.6625	Remote Similarity	NPD4695	Discontinued
0.6552	Remote Similarity	NPD6411	Approved
0.65	Remote Similarity	NPD4195	Approved
0.6477	Remote Similarity	NPD4202	Approved
0.6438	Remote Similarity	NPD7331	Phase 2
0.6429	Remote Similarity	NPD1696	Phase 3
0.6404	Remote Similarity	NPD7748	Approved
0.6375	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD4732	Discontinued
0.6364	Remote Similarity	NPD7087	Discontinued
0.6322	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6322	Remote Similarity	NPD6101	Approved
0.6322	Remote Similarity	NPD4753	Phase 2
0.631	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6265	Remote Similarity	NPD4223	Phase 3
0.6265	Remote Similarity	NPD4221	Approved
0.6264	Remote Similarity	NPD4697	Phase 3
0.6264	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6264	Remote Similarity	NPD5222	Approved
0.6264	Remote Similarity	NPD5221	Approved
0.625	Remote Similarity	NPD7136	Phase 2
0.6235	Remote Similarity	NPD5329	Approved
0.6235	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.622	Remote Similarity	NPD4822	Approved
0.622	Remote Similarity	NPD4820	Approved
0.622	Remote Similarity	NPD4821	Approved
0.622	Remote Similarity	NPD4819	Approved
0.6196	Remote Similarity	NPD7902	Approved
0.6196	Remote Similarity	NPD5173	Approved
0.6196	Remote Similarity	NPD4755	Approved
0.619	Remote Similarity	NPD5331	Approved
0.619	Remote Similarity	NPD5332	Approved
0.619	Remote Similarity	NPD5362	Discontinued
0.6184	Remote Similarity	NPD791	Approved
0.6184	Remote Similarity	NPD15	Approved
0.618	Remote Similarity	NPD7637	Suspended
0.6173	Remote Similarity	NPD4268	Approved
0.6173	Remote Similarity	NPD4271	Approved
0.6163	Remote Similarity	NPD7334	Approved
0.6163	Remote Similarity	NPD6684	Approved
0.6163	Remote Similarity	NPD5330	Approved
0.6163	Remote Similarity	NPD7146	Approved
0.6163	Remote Similarity	NPD7521	Approved
0.6163	Remote Similarity	NPD6409	Approved
0.6145	Remote Similarity	NPD4790	Discontinued
0.6145	Remote Similarity	NPD5369	Approved
0.6129	Remote Similarity	NPD7638	Approved
0.6129	Remote Similarity	NPD5290	Discontinued
0.6129	Remote Similarity	NPD4225	Approved
0.6125	Remote Similarity	NPD1346	Approved
0.6118	Remote Similarity	NPD4197	Approved
0.6111	Remote Similarity	NPD5779	Approved
0.6111	Remote Similarity	NPD5778	Approved
0.6081	Remote Similarity	NPD7341	Phase 2
0.6071	Remote Similarity	NPD4270	Approved
0.6071	Remote Similarity	NPD4269	Approved
0.6064	Remote Similarity	NPD4700	Approved
0.6064	Remote Similarity	NPD5285	Approved
0.6064	Remote Similarity	NPD7639	Approved
0.6064	Remote Similarity	NPD4696	Approved
0.6064	Remote Similarity	NPD5286	Approved
0.6064	Remote Similarity	NPD7640	Approved
0.6032	Remote Similarity	NPD4265	Approved
0.6024	Remote Similarity	NPD5368	Approved
0.6024	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6023	Remote Similarity	NPD6903	Approved
0.6023	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6022	Remote Similarity	NPD6083	Phase 2
0.6022	Remote Similarity	NPD6084	Phase 2
0.6	Remote Similarity	NPD4788	Approved
0.6	Remote Similarity	NPD8262	Approved
0.6	Remote Similarity	NPD5223	Approved
0.6	Remote Similarity	NPD7154	Phase 3
0.6	Remote Similarity	NPD8039	Approved
0.5978	Remote Similarity	NPD4629	Approved
0.5978	Remote Similarity	NPD5210	Approved
0.5977	Remote Similarity	NPD4623	Approved
0.5977	Remote Similarity	NPD4694	Approved
0.5977	Remote Similarity	NPD4519	Discontinued
0.5977	Remote Similarity	NPD4689	Approved
0.5977	Remote Similarity	NPD4138	Approved
0.5977	Remote Similarity	NPD4693	Phase 3
0.5977	Remote Similarity	NPD5205	Approved
0.5977	Remote Similarity	NPD5280	Approved
0.5977	Remote Similarity	NPD4690	Approved
0.5977	Remote Similarity	NPD4688	Approved
0.5977	Remote Similarity	NPD5690	Phase 2
0.5976	Remote Similarity	NPD3617	Approved
0.5974	Remote Similarity	NPD1082	Approved
0.5955	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.5955	Remote Similarity	NPD6051	Approved
0.5946	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.5938	Remote Similarity	NPD5226	Approved
0.5938	Remote Similarity	NPD5224	Approved
0.5938	Remote Similarity	NPD384	Approved
0.5938	Remote Similarity	NPD5225	Approved
0.5938	Remote Similarity	NPD5211	Phase 2
0.5938	Remote Similarity	NPD4633	Approved
0.5938	Remote Similarity	NPD385	Approved
0.5918	Remote Similarity	NPD7128	Approved
0.5918	Remote Similarity	NPD6675	Approved
0.5918	Remote Similarity	NPD5739	Approved
0.5918	Remote Similarity	NPD6402	Approved
0.5915	Remote Similarity	NPD287	Approved
0.589	Remote Similarity	NPD4191	Approved
0.589	Remote Similarity	NPD4193	Approved
0.589	Remote Similarity	NPD4194	Approved
0.589	Remote Similarity	NPD4192	Approved
0.5889	Remote Similarity	NPD5785	Approved
0.5882	Remote Similarity	NPD6435	Approved
0.5876	Remote Similarity	NPD5175	Approved
0.5876	Remote Similarity	NPD4754	Approved
0.5876	Remote Similarity	NPD5174	Approved
0.587	Remote Similarity	NPD7900	Approved
0.587	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5862	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.5862	Remote Similarity	NPD5363	Approved
0.5844	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.5843	Remote Similarity	NPD4723	Approved
0.5843	Remote Similarity	NPD5737	Approved
0.5843	Remote Similarity	NPD4722	Approved
0.5843	Remote Similarity	NPD6672	Approved
0.5843	Remote Similarity	NPD4518	Approved
0.5833	Remote Similarity	NPD4252	Approved
0.5816	Remote Similarity	NPD5141	Approved
0.5806	Remote Similarity	NPD1799	Clinical (unspecified phase)
0.5806	Remote Similarity	NPD5695	Phase 3
0.58	Remote Similarity	NPD6881	Approved
0.58	Remote Similarity	NPD6899	Approved
0.58	Remote Similarity	NPD7320	Approved
0.5795	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5795	Remote Similarity	NPD5786	Approved
0.5769	Remote Similarity	NPD4137	Phase 3
0.5769	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.5765	Remote Similarity	NPD4139	Approved
0.5765	Remote Similarity	NPD4692	Approved
0.5758	Remote Similarity	NPD4768	Approved
0.5758	Remote Similarity	NPD4767	Approved
0.5747	Remote Similarity	NPD5766	Clinical (unspecified phase)
0.5743	Remote Similarity	NPD6373	Approved
0.5743	Remote Similarity	NPD6372	Approved
0.5733	Remote Similarity	NPD3197	Phase 1

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