NPASS Compound

Structure

CID149680 OpenBabel06191715522D 21 22 0 0 1 0 0 0 0 0999 V2000 3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 3.5000 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 -1.3660 -2.3660 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 2.5981 3.5000 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 1.7321 2.0000 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 0.8660 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 -1.7321 -1.0000 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 -0.3660 -2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 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 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 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 -0.8660 -3.2321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 2 0 0 0 0 2 15 1 0 0 0 0 3 16 2 0 0 0 0 6 15 1 0 0 0 0 7 12 1 0 0 0 0 7 13 1 0 0 0 0 8 10 1 0 0 0 0 8 15 2 0 0 0 0 9 11 1 0 0 0 0 9 16 1 0 0 0 0 10 17 1 0 0 0 0 11 18 1 0 0 0 0 12 19 1 0 0 0 0 13 20 1 0 0 0 0 14 19 1 0 0 0 0 14 21 1 0 0 0 0 16 17 1 0 0 0 0 17 20 1 1 0 0 0 18 19 1 1 0 0 0 18 20 1 0 0 0 0 19 4 1 1 0 0 0 20 5 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	288.25
Volume:	338.244
LogP:	4.015
LogD:	3.964
LogS:	-4.432
# Rotatable Bonds:	4
TPSA:	20.23
# H-Bond Aceptor:	1
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.551
Synthetic Accessibility Score:	4.413
Fsp3:	0.7
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:	-4.667
MDCK Permeability:	1.80344759428408e-05
Pgp-inhibitor:	0.053
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.574
30% Bioavailability (F30%):	0.36

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.43
Plasma Protein Binding (PPB):	89.19107818603516%
Volume Distribution (VD):	1.471
Pgp-substrate:	10.207926750183105%

ADMET: Metabolism

CYP1A2-inhibitor:	0.181
CYP1A2-substrate:	0.403
CYP2C19-inhibitor:	0.127
CYP2C19-substrate:	0.893
CYP2C9-inhibitor:	0.199
CYP2C9-substrate:	0.284
CYP2D6-inhibitor:	0.089
CYP2D6-substrate:	0.887
CYP3A4-inhibitor:	0.833
CYP3A4-substrate:	0.409

ADMET: Excretion

Clearance (CL):	7.318
Half-life (T1/2):	0.464

ADMET: Toxicity

hERG Blockers:	0.012
Human Hepatotoxicity (H-HT):	0.13
Drug-inuced Liver Injury (DILI):	0.038
AMES Toxicity:	0.012
Rat Oral Acute Toxicity:	0.104
Maximum Recommended Daily Dose:	0.925
Skin Sensitization:	0.735
Carcinogencity:	0.135
Eye Corrosion:	0.749
Eye Irritation:	0.967
Respiratory Toxicity:	0.939

Download Data

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

Natural Product: NPC149680

Natural Product ID:	NPC149680
*Common Name:**	KDNYVXLYMQKQHH-LMMWYNSXSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	KDNYVXLYMQKQHH-LMMWYNSXSA-N
Standard InCHI:	InChI=1S/C20H32O/c1-6-15(2)8-10-17-16(3)9-11-18-19(4,14-21)12-7-13-20(17,18)5/h6,8,17-18,21H,1,3,7,9-14H2,2,4-5H3/b15-8+/t17-,18-,19-,20+/m0/s1
SMILES:	C=C/C(=C/C[C@H]1C(=C)CC[C@H]2[C@@](C)(CCC[C@]12C)CO)/C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3402736
PubChem CID:	NA
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
NPO1994	Panax stipuleanatus	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20951582]
NPO3881	Erucastrum gallicum	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1994	Panax stipuleanatus	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17373	Cunninghamia lanceolata	Species	Cupressaceae	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
GI50	1

Activity Type	# Activity
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI50	=	35030.0	nM	PMID[504553]

☑ 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 NPC149680 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	166
0.1-0.2	1280
0.2-0.3	7603
0.3-0.4	16674
0.4-0.5	8750
0.5-0.6	5537
0.6-0.7	2132
0.7-0.8	467
0.8-0.85	64
0.85-0.9	17
0.9-0.95	6
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9375	High Similarity	NPC32055
0.9219	High Similarity	NPC197805
0.9104	High Similarity	NPC68443
0.9077	High Similarity	NPC216460
0.9062	High Similarity	NPC222366
0.9062	High Similarity	NPC476039
0.9062	High Similarity	NPC286669
0.8923	High Similarity	NPC68703
0.8923	High Similarity	NPC69649
0.8806	High Similarity	NPC145498
0.8788	High Similarity	NPC160209
0.8676	High Similarity	NPC242001
0.8657	High Similarity	NPC476431
0.8615	High Similarity	NPC163678
0.8571	High Similarity	NPC471468
0.8551	High Similarity	NPC182717
0.8551	High Similarity	NPC471799
0.8529	High Similarity	NPC49422
0.8529	High Similarity	NPC9161
0.8507	High Similarity	NPC208999
0.8485	Intermediate Similarity	NPC476406
0.8472	Intermediate Similarity	NPC76931
0.8472	Intermediate Similarity	NPC307965
0.8472	Intermediate Similarity	NPC18603
0.8462	Intermediate Similarity	NPC225415
0.8451	Intermediate Similarity	NPC106432
0.8429	Intermediate Similarity	NPC27395
0.8429	Intermediate Similarity	NPC91858
0.8429	Intermediate Similarity	NPC477138
0.8429	Intermediate Similarity	NPC471797
0.8429	Intermediate Similarity	NPC329090
0.8429	Intermediate Similarity	NPC243342
0.8406	Intermediate Similarity	NPC167706
0.8382	Intermediate Similarity	NPC167272
0.8382	Intermediate Similarity	NPC269877
0.831	Intermediate Similarity	NPC328104
0.831	Intermediate Similarity	NPC319090
0.831	Intermediate Similarity	NPC291503
0.8286	Intermediate Similarity	NPC474743
0.8261	Intermediate Similarity	NPC34834
0.8209	Intermediate Similarity	NPC279434
0.8194	Intermediate Similarity	NPC315261
0.8194	Intermediate Similarity	NPC134330
0.8194	Intermediate Similarity	NPC129165
0.8194	Intermediate Similarity	NPC113733
0.8182	Intermediate Similarity	NPC290367
0.8169	Intermediate Similarity	NPC201048
0.8169	Intermediate Similarity	NPC306727
0.8169	Intermediate Similarity	NPC476366
0.8169	Intermediate Similarity	NPC100334
0.8154	Intermediate Similarity	NPC41160
0.8143	Intermediate Similarity	NPC110799
0.8116	Intermediate Similarity	NPC9942
0.8088	Intermediate Similarity	NPC171225
0.8082	Intermediate Similarity	NPC471798
0.8082	Intermediate Similarity	NPC91594
0.806	Intermediate Similarity	NPC27243
0.806	Intermediate Similarity	NPC64123
0.806	Intermediate Similarity	NPC476737
0.8056	Intermediate Similarity	NPC288035
0.8056	Intermediate Similarity	NPC477923
0.8056	Intermediate Similarity	NPC136188
0.8056	Intermediate Similarity	NPC134847
0.8056	Intermediate Similarity	NPC28657
0.8056	Intermediate Similarity	NPC32832
0.8056	Intermediate Similarity	NPC285893
0.8056	Intermediate Similarity	NPC141071
0.8056	Intermediate Similarity	NPC66566
0.8056	Intermediate Similarity	NPC162742
0.8056	Intermediate Similarity	NPC257347
0.8056	Intermediate Similarity	NPC471723
0.8056	Intermediate Similarity	NPC304309
0.8056	Intermediate Similarity	NPC230301
0.8056	Intermediate Similarity	NPC476844
0.8056	Intermediate Similarity	NPC22105
0.8028	Intermediate Similarity	NPC474140
0.8028	Intermediate Similarity	NPC130665
0.8	Intermediate Similarity	NPC475728
0.7973	Intermediate Similarity	NPC83351
0.7973	Intermediate Similarity	NPC318136
0.7973	Intermediate Similarity	NPC167891
0.7973	Intermediate Similarity	NPC72507
0.7973	Intermediate Similarity	NPC205455
0.7973	Intermediate Similarity	NPC186191
0.7971	Intermediate Similarity	NPC94192
0.7945	Intermediate Similarity	NPC265328
0.7945	Intermediate Similarity	NPC189883
0.7945	Intermediate Similarity	NPC122418
0.7945	Intermediate Similarity	NPC106364
0.7945	Intermediate Similarity	NPC300324
0.7945	Intermediate Similarity	NPC477925
0.7945	Intermediate Similarity	NPC107059
0.7945	Intermediate Similarity	NPC321381
0.7945	Intermediate Similarity	NPC470362
0.7945	Intermediate Similarity	NPC321016
0.7945	Intermediate Similarity	NPC274079
0.7945	Intermediate Similarity	NPC247325
0.7945	Intermediate Similarity	NPC30590
0.7945	Intermediate Similarity	NPC244488
0.7945	Intermediate Similarity	NPC27765
0.7945	Intermediate Similarity	NPC120098
0.7945	Intermediate Similarity	NPC237460
0.7945	Intermediate Similarity	NPC240604
0.7945	Intermediate Similarity	NPC470749
0.7945	Intermediate Similarity	NPC253190
0.7945	Intermediate Similarity	NPC290598
0.7945	Intermediate Similarity	NPC265588
0.7922	Intermediate Similarity	NPC82538
0.7922	Intermediate Similarity	NPC237795
0.7917	Intermediate Similarity	NPC469533
0.7917	Intermediate Similarity	NPC3753
0.7917	Intermediate Similarity	NPC469593
0.7917	Intermediate Similarity	NPC469534
0.7917	Intermediate Similarity	NPC237591
0.7867	Intermediate Similarity	NPC100906
0.7867	Intermediate Similarity	NPC474113
0.7857	Intermediate Similarity	NPC471560
0.7857	Intermediate Similarity	NPC474248
0.7838	Intermediate Similarity	NPC318495
0.7838	Intermediate Similarity	NPC34177
0.7838	Intermediate Similarity	NPC155986
0.7838	Intermediate Similarity	NPC90979
0.7838	Intermediate Similarity	NPC198968
0.7838	Intermediate Similarity	NPC34019
0.7838	Intermediate Similarity	NPC40394
0.7838	Intermediate Similarity	NPC477924
0.7838	Intermediate Similarity	NPC470711
0.7838	Intermediate Similarity	NPC157996
0.7838	Intermediate Similarity	NPC472805
0.7838	Intermediate Similarity	NPC101475
0.7838	Intermediate Similarity	NPC130136
0.7838	Intermediate Similarity	NPC470758
0.7826	Intermediate Similarity	NPC114651
0.7821	Intermediate Similarity	NPC474493
0.7812	Intermediate Similarity	NPC11130
0.7808	Intermediate Similarity	NPC69383
0.7808	Intermediate Similarity	NPC313179
0.7808	Intermediate Similarity	NPC171148
0.7808	Intermediate Similarity	NPC34700
0.7808	Intermediate Similarity	NPC138374
0.7763	Intermediate Similarity	NPC324772
0.7763	Intermediate Similarity	NPC164840
0.7763	Intermediate Similarity	NPC241290
0.7763	Intermediate Similarity	NPC234193
0.7763	Intermediate Similarity	NPC96362
0.7763	Intermediate Similarity	NPC287749
0.7763	Intermediate Similarity	NPC209944
0.7746	Intermediate Similarity	NPC92801
0.7733	Intermediate Similarity	NPC196753
0.7733	Intermediate Similarity	NPC253807
0.7733	Intermediate Similarity	NPC239098
0.7733	Intermediate Similarity	NPC244385
0.7733	Intermediate Similarity	NPC6978
0.7733	Intermediate Similarity	NPC302041
0.7733	Intermediate Similarity	NPC477514
0.7733	Intermediate Similarity	NPC285761
0.7733	Intermediate Similarity	NPC167037
0.7733	Intermediate Similarity	NPC87604
0.7733	Intermediate Similarity	NPC474989
0.7733	Intermediate Similarity	NPC99168
0.7733	Intermediate Similarity	NPC230295
0.7733	Intermediate Similarity	NPC473943
0.7733	Intermediate Similarity	NPC300499
0.7733	Intermediate Similarity	NPC85346
0.7733	Intermediate Similarity	NPC476314
0.7733	Intermediate Similarity	NPC158662
0.7733	Intermediate Similarity	NPC474216
0.7733	Intermediate Similarity	NPC11908
0.7733	Intermediate Similarity	NPC22955
0.7733	Intermediate Similarity	NPC312328
0.7733	Intermediate Similarity	NPC477522
0.7733	Intermediate Similarity	NPC470396
0.7733	Intermediate Similarity	NPC65897
0.7733	Intermediate Similarity	NPC98386
0.7733	Intermediate Similarity	NPC138621
0.7714	Intermediate Similarity	NPC96484
0.7714	Intermediate Similarity	NPC471238
0.7714	Intermediate Similarity	NPC2648
0.7703	Intermediate Similarity	NPC63958
0.7703	Intermediate Similarity	NPC46160
0.7703	Intermediate Similarity	NPC202642
0.7703	Intermediate Similarity	NPC96319
0.7692	Intermediate Similarity	NPC474789
0.7692	Intermediate Similarity	NPC470384
0.7692	Intermediate Similarity	NPC52108
0.7692	Intermediate Similarity	NPC312480
0.7692	Intermediate Similarity	NPC10017
0.7681	Intermediate Similarity	NPC250977
0.7681	Intermediate Similarity	NPC202017
0.7671	Intermediate Similarity	NPC78527
0.7662	Intermediate Similarity	NPC249423
0.7662	Intermediate Similarity	NPC142163
0.7662	Intermediate Similarity	NPC121984
0.7662	Intermediate Similarity	NPC320525
0.7662	Intermediate Similarity	NPC264245
0.7662	Intermediate Similarity	NPC47761
0.7662	Intermediate Similarity	NPC476646
0.7656	Intermediate Similarity	NPC264779
0.7656	Intermediate Similarity	NPC39068
0.7647	Intermediate Similarity	NPC107540

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 NPC149680 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	162
0.1-0.2	1473
0.2-0.3	4191
0.3-0.4	2318
0.4-0.5	661
0.5-0.6	233
0.6-0.7	73
0.7-0.8	30
0.8-0.85	9
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8529	High Similarity	NPD7143	Approved
0.8529	High Similarity	NPD7144	Approved
0.8429	Intermediate Similarity	NPD6924	Approved
0.8429	Intermediate Similarity	NPD6926	Approved
0.8406	Intermediate Similarity	NPD7150	Approved
0.8406	Intermediate Similarity	NPD7151	Approved
0.8406	Intermediate Similarity	NPD7152	Approved
0.8382	Intermediate Similarity	NPD6923	Approved
0.8382	Intermediate Similarity	NPD6922	Approved
0.8194	Intermediate Similarity	NPD6933	Approved
0.8056	Intermediate Similarity	NPD6942	Approved
0.8056	Intermediate Similarity	NPD7339	Approved
0.7867	Intermediate Similarity	NPD6929	Approved
0.7838	Intermediate Similarity	NPD6932	Approved
0.7808	Intermediate Similarity	NPD8264	Approved
0.7763	Intermediate Similarity	NPD6930	Phase 2
0.7763	Intermediate Similarity	NPD7509	Discontinued
0.7763	Intermediate Similarity	NPD6931	Approved
0.7733	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD7145	Approved
0.7703	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7671	Intermediate Similarity	NPD4784	Approved
0.7671	Intermediate Similarity	NPD4785	Approved
0.7639	Intermediate Similarity	NPD4243	Approved
0.7632	Intermediate Similarity	NPD7645	Phase 2
0.76	Intermediate Similarity	NPD5776	Phase 2
0.76	Intermediate Similarity	NPD6925	Approved
0.7532	Intermediate Similarity	NPD7525	Registered
0.7532	Intermediate Similarity	NPD7332	Phase 2
0.7532	Intermediate Similarity	NPD7514	Phase 3
0.7468	Intermediate Similarity	NPD6695	Phase 3
0.7436	Intermediate Similarity	NPD6902	Approved
0.7403	Intermediate Similarity	NPD6683	Phase 2
0.7385	Intermediate Similarity	NPD4219	Approved
0.7375	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD6893	Approved
0.7215	Intermediate Similarity	NPD6898	Phase 1
0.716	Intermediate Similarity	NPD4786	Approved
0.7125	Intermediate Similarity	NPD3667	Approved
0.7108	Intermediate Similarity	NPD7750	Discontinued
0.7108	Intermediate Similarity	NPD7524	Approved
0.7105	Intermediate Similarity	NPD5275	Approved
0.7105	Intermediate Similarity	NPD4190	Phase 3
0.6988	Remote Similarity	NPD5279	Phase 3
0.697	Remote Similarity	NPD342	Phase 1
0.6962	Remote Similarity	NPD4195	Approved
0.6951	Remote Similarity	NPD3665	Phase 1
0.6951	Remote Similarity	NPD3133	Approved
0.6951	Remote Similarity	NPD3666	Approved
0.6786	Remote Similarity	NPD3618	Phase 1
0.6782	Remote Similarity	NPD6079	Approved
0.6782	Remote Similarity	NPD7087	Discontinued
0.6744	Remote Similarity	NPD5328	Approved
0.6706	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4695	Discontinued
0.6667	Remote Similarity	NPD7136	Phase 2
0.6591	Remote Similarity	NPD6411	Approved
0.6591	Remote Similarity	NPD7515	Phase 2
0.6591	Remote Similarity	NPD7637	Suspended
0.6562	Remote Similarity	NPD8262	Approved
0.6552	Remote Similarity	NPD4753	Phase 2
0.6506	Remote Similarity	NPD4223	Phase 3
0.6506	Remote Similarity	NPD4221	Approved
0.6471	Remote Similarity	NPD5329	Approved
0.6463	Remote Similarity	NPD4748	Discontinued
0.6463	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD4788	Approved
0.641	Remote Similarity	NPD4732	Discontinued
0.6395	Remote Similarity	NPD5280	Approved
0.6395	Remote Similarity	NPD4623	Approved
0.6395	Remote Similarity	NPD4519	Discontinued
0.6395	Remote Similarity	NPD4694	Approved
0.6389	Remote Similarity	NPD368	Approved
0.6374	Remote Similarity	NPD4629	Approved
0.6374	Remote Similarity	NPD5210	Approved
0.6364	Remote Similarity	NPD6101	Approved
0.6364	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6353	Remote Similarity	NPD3668	Phase 3
0.6353	Remote Similarity	NPD4197	Approved
0.6333	Remote Similarity	NPD6399	Phase 3
0.6333	Remote Similarity	NPD4202	Approved
0.631	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6304	Remote Similarity	NPD5222	Approved
0.6304	Remote Similarity	NPD5221	Approved
0.6304	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6279	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6264	Remote Similarity	NPD7748	Approved
0.625	Remote Similarity	NPD8039	Approved
0.6237	Remote Similarity	NPD5173	Approved
0.6237	Remote Similarity	NPD6084	Phase 2
0.6237	Remote Similarity	NPD6083	Phase 2
0.6222	Remote Similarity	NPD5284	Approved
0.6222	Remote Similarity	NPD5281	Approved
0.622	Remote Similarity	NPD3617	Approved
0.6216	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD5330	Approved
0.6207	Remote Similarity	NPD7521	Approved
0.6207	Remote Similarity	NPD4688	Approved
0.6207	Remote Similarity	NPD5690	Phase 2
0.6207	Remote Similarity	NPD6409	Approved
0.6207	Remote Similarity	NPD5205	Approved
0.6207	Remote Similarity	NPD4138	Approved
0.6207	Remote Similarity	NPD6684	Approved
0.6207	Remote Similarity	NPD7146	Approved
0.6207	Remote Similarity	NPD4689	Approved
0.6207	Remote Similarity	NPD4690	Approved
0.6207	Remote Similarity	NPD4693	Phase 3
0.6207	Remote Similarity	NPD7334	Approved
0.617	Remote Similarity	NPD5290	Discontinued
0.617	Remote Similarity	NPD7638	Approved
0.6164	Remote Similarity	NPD4192	Approved
0.6164	Remote Similarity	NPD4193	Approved
0.6164	Remote Similarity	NPD4191	Approved
0.6164	Remote Similarity	NPD4194	Approved
0.6154	Remote Similarity	NPD5778	Approved
0.6154	Remote Similarity	NPD5779	Approved
0.6129	Remote Similarity	NPD1799	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD4697	Phase 3
0.6125	Remote Similarity	NPD4058	Approved
0.6111	Remote Similarity	NPD4096	Approved
0.6105	Remote Similarity	NPD5285	Approved
0.6105	Remote Similarity	NPD5286	Approved
0.6105	Remote Similarity	NPD7639	Approved
0.6105	Remote Similarity	NPD4696	Approved
0.6105	Remote Similarity	NPD7640	Approved
0.6067	Remote Similarity	NPD6672	Approved
0.6067	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6067	Remote Similarity	NPD4722	Approved
0.6067	Remote Similarity	NPD4723	Approved
0.6067	Remote Similarity	NPD4518	Approved
0.6067	Remote Similarity	NPD5737	Approved
0.6067	Remote Similarity	NPD6903	Approved
0.6064	Remote Similarity	NPD4755	Approved
0.6064	Remote Similarity	NPD7902	Approved
0.6042	Remote Similarity	NPD5223	Approved
0.6024	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6023	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6051	Approved
0.6	Remote Similarity	NPD4225	Approved
0.5979	Remote Similarity	NPD5225	Approved
0.5979	Remote Similarity	NPD4633	Approved
0.5979	Remote Similarity	NPD5224	Approved
0.5979	Remote Similarity	NPD5226	Approved
0.5979	Remote Similarity	NPD5211	Phase 2
0.5976	Remote Similarity	NPD1346	Approved
0.5938	Remote Similarity	NPD4700	Approved
0.5934	Remote Similarity	NPD4001	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD5733	Approved
0.5926	Remote Similarity	NPD4687	Approved
0.5921	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.5918	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.5918	Remote Similarity	NPD5175	Approved
0.5918	Remote Similarity	NPD5174	Approved
0.5909	Remote Similarity	NPD1696	Phase 3
0.5897	Remote Similarity	NPD6705	Phase 1
0.5897	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.5875	Remote Similarity	NPD5276	Approved
0.5859	Remote Similarity	NPD5141	Approved
0.5851	Remote Similarity	NPD5695	Phase 3
0.5846	Remote Similarity	NPD4265	Approved
0.5844	Remote Similarity	NPD7331	Phase 2
0.5843	Remote Similarity	NPD6098	Approved
0.5842	Remote Similarity	NPD6881	Approved
0.5842	Remote Similarity	NPD6899	Approved
0.5833	Remote Similarity	NPD5696	Approved
0.5823	Remote Similarity	NPD791	Approved
0.5823	Remote Similarity	NPD4137	Phase 3
0.5823	Remote Similarity	NPD15	Approved
0.5823	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.5814	Remote Similarity	NPD4139	Approved
0.5814	Remote Similarity	NPD4692	Approved
0.5806	Remote Similarity	NPD5133	Approved
0.58	Remote Similarity	NPD6640	Phase 3
0.58	Remote Similarity	NPD7128	Approved
0.58	Remote Similarity	NPD5739	Approved
0.58	Remote Similarity	NPD6402	Approved
0.58	Remote Similarity	NPD6675	Approved
0.5778	Remote Similarity	NPD3573	Approved
0.5773	Remote Similarity	NPD6404	Discontinued
0.5761	Remote Similarity	NPD5207	Approved
0.5758	Remote Similarity	NPD384	Approved
0.5758	Remote Similarity	NPD4754	Approved
0.5758	Remote Similarity	NPD385	Approved
0.575	Remote Similarity	NPD4245	Approved
0.575	Remote Similarity	NPD4747	Approved
0.575	Remote Similarity	NPD4691	Approved
0.575	Remote Similarity	NPD4787	Phase 1
0.575	Remote Similarity	NPD4789	Approved
0.575	Remote Similarity	NPD4244	Approved
0.575	Remote Similarity	NPD6938	Clinical (unspecified phase)
0.575	Remote Similarity	NPD6939	Phase 2
0.5745	Remote Similarity	NPD5771	Approved
0.5745	Remote Similarity	NPD7900	Approved
0.5745	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5743	Remote Similarity	NPD5697	Approved
0.5743	Remote Similarity	NPD6412	Phase 2
0.5728	Remote Similarity	NPD7102	Approved
0.5728	Remote Similarity	NPD7290	Approved
0.5728	Remote Similarity	NPD6883	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