NPASS Compound

Structure

CID167103 OpenBabel06191715542D 33 37 0 0 1 0 0 0 0 0999 V2000 -0.6008 -2.8809 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6669 -4.0210 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2914 2.8774 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1392 2.3875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4678 -0.5049 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0251 0.9645 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8222 -1.4250 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6450 -0.9503 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9646 -2.4518 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6458 1.8987 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8230 1.4240 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3503 -1.5842 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1124 1.4230 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1121 0.4738 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6441 0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8219 0.4752 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3621 -3.0850 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0204 -2.3531 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0003 -0.9499 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4683 1.4235 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6453 -0.0005 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8225 -1.4245 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4663 -0.4742 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0005 1.8988 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2911 1.8982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4680 0.4742 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8228 0.4747 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6444 -0.9494 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 3.1722 -1.1091 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6632 0.4545 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9280 2.0964 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6360 2.6041 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 17 2 0 0 0 0 2 17 1 0 0 0 0 3 25 1 0 0 0 0 4 25 1 0 0 0 0 6 27 1 0 0 0 0 7 8 1 0 0 0 0 7 19 1 0 0 0 0 8 21 1 0 0 0 0 9 12 1 0 0 0 0 9 18 1 0 0 0 0 10 11 1 0 0 0 0 10 20 1 0 0 0 0 11 27 1 0 0 0 0 12 28 1 0 0 0 0 13 14 2 0 0 0 0 13 25 1 0 0 0 0 14 26 1 0 0 0 0 15 16 1 0 0 0 0 15 28 1 0 0 0 0 16 29 1 0 0 0 0 18 17 1 1 0 0 0 18 22 1 0 0 0 0 19 22 1 0 0 0 0 19 29 1 1 0 0 0 20 25 1 0 0 0 0 20 26 1 6 0 0 0 21 26 1 6 0 0 0 21 27 1 0 0 0 0 22 28 1 6 0 0 0 23 30 2 0 0 0 0 23 31 1 0 0 0 0 24 32 2 0 0 0 0 24 33 1 0 0 0 0 26 5 1 6 0 0 0 27 29 1 1 0 0 0 28 23 1 6 0 0 0 29 24 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	454.31
Volume:	491.973
LogP:	6.303
LogD:	4.575
LogS:	-3.945
# Rotatable Bonds:	3
TPSA:	74.6
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.473
Synthetic Accessibility Score:	5.073
Fsp3:	0.793
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:	-5.887
MDCK Permeability:	7.252638624777319e-06
Pgp-inhibitor:	0.0
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.011
30% Bioavailability (F30%):	0.894

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.108
Plasma Protein Binding (PPB):	89.6858901977539%
Volume Distribution (VD):	0.487
Pgp-substrate:	8.67452621459961%

ADMET: Metabolism

CYP1A2-inhibitor:	0.01
CYP1A2-substrate:	0.468
CYP2C19-inhibitor:	0.011
CYP2C19-substrate:	0.808
CYP2C9-inhibitor:	0.153
CYP2C9-substrate:	0.471
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.142
CYP3A4-inhibitor:	0.241
CYP3A4-substrate:	0.173

ADMET: Excretion

Clearance (CL):	0.969
Half-life (T1/2):	0.265

ADMET: Toxicity

hERG Blockers:	0.015
Human Hepatotoxicity (H-HT):	0.49
Drug-inuced Liver Injury (DILI):	0.006
AMES Toxicity:	0.002
Rat Oral Acute Toxicity:	0.224
Maximum Recommended Daily Dose:	0.674
Skin Sensitization:	0.054
Carcinogencity:	0.136
Eye Corrosion:	0.233
Eye Irritation:	0.106
Respiratory Toxicity:	0.923

Download Data

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

Natural Product: NPC167103

Natural Product ID:	NPC167103
*Common Name:**	Ceanothenic Acid
IUPAC Name:	n.a.
Synonyms:	Ceanothenic Acid
Standard InCHIKey:	CMDOQXSBVNWCEM-AKDRKZOISA-N
Standard InCHI:	InChI=1S/C29H42O4/c1-17(2)18-9-12-28(23(30)31)15-16-29(24(32)33)19(22(18)28)7-8-21-26(5)14-13-25(3,4)20(26)10-11-27(21,29)6/h13-14,18-22H,1,7-12,15-16H2,2-6H3,(H,30,31)(H,32,33)/t18-,19+,20-,21+,22+,26-,27+,28-,29+/m0/s1
SMILES:	C=C(C)[C@@H]1CC[C@@]2(CC[C@@]3([C@H](CC[C@@H]4[C@@]5(C)C=CC(C)(C)[C@@H]5CC[C@@]34C)[C@@H]12)C(=O)O)C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2151978
PubChem CID:	71451218
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
NPO4792	Ziziphus mauritiana	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22989532]
NPO5986	Ziziphus jujuba	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27617953]
NPO5986	Ziziphus jujuba	Species	Rhamnaceae	Eukaryota	Roots	n.a.	n.a.	PMID[28257196]
NPO5986	Ziziphus jujuba	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4792	Ziziphus mauritiana	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5986	Ziziphus jujuba	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4792	Ziziphus mauritiana	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4792	Ziziphus mauritiana	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5986	Ziziphus jujuba	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5986	Ziziphus jujuba	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]

☑ 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	4

Activity Type	# Activity
Cell Line	2
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT547	Cell Line	BGC-823	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[555270]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	7.55	ug.mL-1	PMID[555270]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IC50	>	20.0	ug.mL-1	PMID[555270]
NPT20	Organism	Candida albicans	Candida albicans	IC50	>	10.0	ug.mL-1	PMID[555270]

☑ 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 NPC167103 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	1109
0.2-0.3	6117
0.3-0.4	16402
0.4-0.5	6625
0.5-0.6	6213
0.6-0.7	4420
0.7-0.8	1518
0.8-0.85	100
0.85-0.9	30
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9091	High Similarity	NPC246445
0.9	High Similarity	NPC147066
0.8987	High Similarity	NPC158846
0.8961	High Similarity	NPC201027
0.8861	High Similarity	NPC260385
0.8861	High Similarity	NPC110094
0.8861	High Similarity	NPC280654
0.8795	High Similarity	NPC29447
0.8795	High Similarity	NPC269638
0.8765	High Similarity	NPC38350
0.8765	High Similarity	NPC201912
0.875	High Similarity	NPC477371
0.875	High Similarity	NPC215843
0.875	High Similarity	NPC199595
0.8734	High Similarity	NPC68828
0.8734	High Similarity	NPC471899
0.8734	High Similarity	NPC66105
0.8734	High Similarity	NPC471897
0.8734	High Similarity	NPC107039
0.8718	High Similarity	NPC279666
0.8718	High Similarity	NPC192540
0.8701	High Similarity	NPC330659
0.8701	High Similarity	NPC244708
0.8701	High Similarity	NPC161187
0.8675	High Similarity	NPC248758
0.8675	High Similarity	NPC472864
0.8675	High Similarity	NPC19849
0.8659	High Similarity	NPC133391
0.8659	High Similarity	NPC320514
0.8659	High Similarity	NPC260956
0.8642	High Similarity	NPC37038
0.8642	High Similarity	NPC104545
0.8608	High Similarity	NPC89294
0.8608	High Similarity	NPC69143
0.8605	High Similarity	NPC262043
0.859	High Similarity	NPC103958
0.859	High Similarity	NPC251970
0.859	High Similarity	NPC161923
0.859	High Similarity	NPC241854
0.859	High Similarity	NPC183503
0.859	High Similarity	NPC283908
0.859	High Similarity	NPC476046
0.8588	High Similarity	NPC128644
0.8588	High Similarity	NPC136948
0.8588	High Similarity	NPC96496
0.8588	High Similarity	NPC236618
0.8554	High Similarity	NPC215893
0.8554	High Similarity	NPC69279
0.8554	High Similarity	NPC83569
0.8554	High Similarity	NPC477852
0.8554	High Similarity	NPC477373
0.8537	High Similarity	NPC221647
0.8537	High Similarity	NPC477372
0.8519	High Similarity	NPC274996
0.8519	High Similarity	NPC192744
0.8519	High Similarity	NPC231431
0.8519	High Similarity	NPC196827
0.8519	High Similarity	NPC16394
0.8481	Intermediate Similarity	NPC476844
0.8471	Intermediate Similarity	NPC186975
0.8471	Intermediate Similarity	NPC155011
0.8471	Intermediate Similarity	NPC472869
0.8452	Intermediate Similarity	NPC194937
0.8452	Intermediate Similarity	NPC164577
0.8452	Intermediate Similarity	NPC472865
0.8452	Intermediate Similarity	NPC476038
0.8415	Intermediate Similarity	NPC477057
0.8391	Intermediate Similarity	NPC475921
0.8391	Intermediate Similarity	NPC474704
0.8391	Intermediate Similarity	NPC66344
0.8391	Intermediate Similarity	NPC474570
0.8372	Intermediate Similarity	NPC142361
0.8372	Intermediate Similarity	NPC167877
0.8372	Intermediate Similarity	NPC474684
0.8354	Intermediate Similarity	NPC237591
0.8354	Intermediate Similarity	NPC3753
0.8354	Intermediate Similarity	NPC255168
0.8353	Intermediate Similarity	NPC283733
0.8333	Intermediate Similarity	NPC168188
0.8333	Intermediate Similarity	NPC470015
0.8333	Intermediate Similarity	NPC200752
0.8333	Intermediate Similarity	NPC97913
0.8333	Intermediate Similarity	NPC160817
0.8315	Intermediate Similarity	NPC267266
0.8315	Intermediate Similarity	NPC277721
0.8315	Intermediate Similarity	NPC470656
0.8313	Intermediate Similarity	NPC274050
0.8313	Intermediate Similarity	NPC162632
0.8313	Intermediate Similarity	NPC267691
0.8313	Intermediate Similarity	NPC278459
0.8313	Intermediate Similarity	NPC232625
0.8313	Intermediate Similarity	NPC263272
0.8313	Intermediate Similarity	NPC471898
0.8313	Intermediate Similarity	NPC142244
0.8295	Intermediate Similarity	NPC471896
0.8276	Intermediate Similarity	NPC472870
0.8276	Intermediate Similarity	NPC117122
0.8272	Intermediate Similarity	NPC212661
0.8272	Intermediate Similarity	NPC471035
0.8256	Intermediate Similarity	NPC80590
0.8235	Intermediate Similarity	NPC165064
0.8235	Intermediate Similarity	NPC96095
0.8235	Intermediate Similarity	NPC156981
0.8228	Intermediate Similarity	NPC36310
0.8228	Intermediate Similarity	NPC279241
0.8214	Intermediate Similarity	NPC69101
0.8214	Intermediate Similarity	NPC296367
0.8214	Intermediate Similarity	NPC251779
0.8202	Intermediate Similarity	NPC86266
0.8202	Intermediate Similarity	NPC110657
0.8202	Intermediate Similarity	NPC154101
0.8202	Intermediate Similarity	NPC189520
0.8202	Intermediate Similarity	NPC204341
0.8202	Intermediate Similarity	NPC212301
0.8182	Intermediate Similarity	NPC290445
0.8182	Intermediate Similarity	NPC36616
0.8182	Intermediate Similarity	NPC476733
0.8182	Intermediate Similarity	NPC128496
0.8182	Intermediate Similarity	NPC215029
0.8171	Intermediate Similarity	NPC179028
0.8171	Intermediate Similarity	NPC321690
0.8171	Intermediate Similarity	NPC321514
0.8161	Intermediate Similarity	NPC93778
0.8161	Intermediate Similarity	NPC159046
0.8161	Intermediate Similarity	NPC233836
0.8161	Intermediate Similarity	NPC187376
0.8148	Intermediate Similarity	NPC20466
0.8148	Intermediate Similarity	NPC309399
0.814	Intermediate Similarity	NPC474537
0.814	Intermediate Similarity	NPC470223
0.814	Intermediate Similarity	NPC123319
0.814	Intermediate Similarity	NPC201655
0.814	Intermediate Similarity	NPC94531
0.814	Intermediate Similarity	NPC311702
0.8132	Intermediate Similarity	NPC476174
0.8132	Intermediate Similarity	NPC279974
0.8125	Intermediate Similarity	NPC166797
0.8118	Intermediate Similarity	NPC472740
0.8118	Intermediate Similarity	NPC245866
0.8118	Intermediate Similarity	NPC70834
0.8118	Intermediate Similarity	NPC310470
0.8118	Intermediate Similarity	NPC471037
0.8111	Intermediate Similarity	NPC470376
0.8111	Intermediate Similarity	NPC470224
0.8111	Intermediate Similarity	NPC470375
0.8111	Intermediate Similarity	NPC107674
0.8111	Intermediate Similarity	NPC141497
0.8111	Intermediate Similarity	NPC170220
0.809	Intermediate Similarity	NPC111585
0.809	Intermediate Similarity	NPC472866
0.809	Intermediate Similarity	NPC126993
0.809	Intermediate Similarity	NPC148414
0.809	Intermediate Similarity	NPC175628
0.8072	Intermediate Similarity	NPC327674
0.8068	Intermediate Similarity	NPC211162
0.8068	Intermediate Similarity	NPC242864
0.8068	Intermediate Similarity	NPC183374
0.8049	Intermediate Similarity	NPC61952
0.8049	Intermediate Similarity	NPC238227
0.8049	Intermediate Similarity	NPC165711
0.8046	Intermediate Similarity	NPC55309
0.8046	Intermediate Similarity	NPC264127
0.8046	Intermediate Similarity	NPC28252
0.8046	Intermediate Similarity	NPC70661
0.8046	Intermediate Similarity	NPC2783
0.8046	Intermediate Similarity	NPC324063
0.8043	Intermediate Similarity	NPC235053
0.8043	Intermediate Similarity	NPC327788
0.8043	Intermediate Similarity	NPC29152
0.8023	Intermediate Similarity	NPC221758
0.8023	Intermediate Similarity	NPC100391
0.8023	Intermediate Similarity	NPC214043
0.8023	Intermediate Similarity	NPC59453
0.8023	Intermediate Similarity	NPC85774
0.8023	Intermediate Similarity	NPC82902
0.8023	Intermediate Similarity	NPC477289
0.8022	Intermediate Similarity	NPC49670
0.8022	Intermediate Similarity	NPC159410
0.8	Intermediate Similarity	NPC26888
0.8	Intermediate Similarity	NPC142683
0.8	Intermediate Similarity	NPC193347
0.8	Intermediate Similarity	NPC476187
0.8	Intermediate Similarity	NPC470113
0.8	Intermediate Similarity	NPC473986
0.8	Intermediate Similarity	NPC240302
0.8	Intermediate Similarity	NPC474018
0.8	Intermediate Similarity	NPC100297
0.7978	Intermediate Similarity	NPC116146
0.7978	Intermediate Similarity	NPC84271
0.7978	Intermediate Similarity	NPC24772
0.7978	Intermediate Similarity	NPC474889
0.7978	Intermediate Similarity	NPC77168
0.7978	Intermediate Similarity	NPC102414
0.7978	Intermediate Similarity	NPC54689
0.7957	Intermediate Similarity	NPC107243
0.7957	Intermediate Similarity	NPC57416
0.7957	Intermediate Similarity	NPC475894
0.7957	Intermediate Similarity	NPC156546
0.7957	Intermediate Similarity	NPC108078
0.7955	Intermediate Similarity	NPC134197

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 NPC167103 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	148
0.1-0.2	1358
0.2-0.3	4188
0.3-0.4	2352
0.4-0.5	619
0.5-0.6	186
0.6-0.7	173
0.7-0.8	126
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8111	Intermediate Similarity	NPD6399	Phase 3
0.8023	Intermediate Similarity	NPD4786	Approved
0.8	Intermediate Similarity	NPD5281	Approved
0.8	Intermediate Similarity	NPD4221	Approved
0.8	Intermediate Similarity	NPD4223	Phase 3
0.8	Intermediate Similarity	NPD5284	Approved
0.7931	Intermediate Similarity	NPD5329	Approved
0.7931	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7865	Intermediate Similarity	NPD5737	Approved
0.7865	Intermediate Similarity	NPD6672	Approved
0.7841	Intermediate Similarity	NPD6098	Approved
0.7816	Intermediate Similarity	NPD4197	Approved
0.7791	Intermediate Similarity	NPD3667	Approved
0.7778	Intermediate Similarity	NPD6080	Approved
0.7778	Intermediate Similarity	NPD6904	Approved
0.7778	Intermediate Similarity	NPD6673	Approved
0.7766	Intermediate Similarity	NPD6083	Phase 2
0.7766	Intermediate Similarity	NPD6084	Phase 2
0.7667	Intermediate Similarity	NPD6903	Approved
0.7667	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD6081	Approved
0.764	Intermediate Similarity	NPD4689	Approved
0.764	Intermediate Similarity	NPD4138	Approved
0.764	Intermediate Similarity	NPD4690	Approved
0.764	Intermediate Similarity	NPD7334	Approved
0.764	Intermediate Similarity	NPD5690	Phase 2
0.764	Intermediate Similarity	NPD4693	Phase 3
0.764	Intermediate Similarity	NPD5205	Approved
0.764	Intermediate Similarity	NPD6409	Approved
0.764	Intermediate Similarity	NPD4688	Approved
0.764	Intermediate Similarity	NPD5330	Approved
0.764	Intermediate Similarity	NPD7146	Approved
0.764	Intermediate Similarity	NPD6684	Approved
0.764	Intermediate Similarity	NPD7521	Approved
0.7614	Intermediate Similarity	NPD3133	Approved
0.7614	Intermediate Similarity	NPD3666	Approved
0.7614	Intermediate Similarity	NPD3665	Phase 1
0.7609	Intermediate Similarity	NPD8034	Phase 2
0.7609	Intermediate Similarity	NPD8035	Phase 2
0.7609	Intermediate Similarity	NPD6079	Approved
0.7609	Intermediate Similarity	NPD7515	Phase 2
0.7582	Intermediate Similarity	NPD5328	Approved
0.7582	Intermediate Similarity	NPD4753	Phase 2
0.7582	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7553	Intermediate Similarity	NPD5695	Phase 3
0.7553	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD3617	Approved
0.75	Intermediate Similarity	NPD4788	Approved
0.75	Intermediate Similarity	NPD5696	Approved
0.75	Intermediate Similarity	NPD5207	Approved
0.7473	Intermediate Similarity	NPD5208	Approved
0.747	Intermediate Similarity	NPD4784	Approved
0.747	Intermediate Similarity	NPD4785	Approved
0.7468	Intermediate Similarity	NPD4224	Phase 2
0.7447	Intermediate Similarity	NPD7748	Approved
0.7444	Intermediate Similarity	NPD5280	Approved
0.7444	Intermediate Similarity	NPD3618	Phase 1
0.7444	Intermediate Similarity	NPD4694	Approved
0.7444	Intermediate Similarity	NPD4519	Discontinued
0.7444	Intermediate Similarity	NPD4623	Approved
0.7444	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD4195	Approved
0.7439	Intermediate Similarity	NPD4243	Approved
0.7419	Intermediate Similarity	NPD6050	Approved
0.7419	Intermediate Similarity	NPD5693	Phase 1
0.7419	Intermediate Similarity	NPD5694	Approved
0.7416	Intermediate Similarity	NPD3668	Phase 3
0.7368	Intermediate Similarity	NPD4629	Approved
0.7368	Intermediate Similarity	NPD5210	Approved
0.7356	Intermediate Similarity	NPD7525	Registered
0.7356	Intermediate Similarity	NPD4695	Discontinued
0.7326	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD7638	Approved
0.7317	Intermediate Similarity	NPD4747	Approved
0.7312	Intermediate Similarity	NPD5692	Phase 3
0.7303	Intermediate Similarity	NPD5362	Discontinued
0.7294	Intermediate Similarity	NPD6117	Approved
0.7292	Intermediate Similarity	NPD5222	Approved
0.7292	Intermediate Similarity	NPD5221	Approved
0.7292	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD4692	Approved
0.7273	Intermediate Similarity	NPD4139	Approved
0.7263	Intermediate Similarity	NPD6001	Approved
0.7262	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD6899	Approved
0.7255	Intermediate Similarity	NPD6881	Approved
0.7255	Intermediate Similarity	NPD7320	Approved
0.7253	Intermediate Similarity	NPD5279	Phase 3
0.7245	Intermediate Similarity	NPD7640	Approved
0.7245	Intermediate Similarity	NPD7639	Approved
0.7245	Intermediate Similarity	NPD6404	Discontinued
0.7228	Intermediate Similarity	NPD6402	Approved
0.7228	Intermediate Similarity	NPD5739	Approved
0.7228	Intermediate Similarity	NPD7128	Approved
0.7228	Intermediate Similarity	NPD6675	Approved
0.7216	Intermediate Similarity	NPD5173	Approved
0.7216	Intermediate Similarity	NPD7902	Approved
0.7209	Intermediate Similarity	NPD6116	Phase 1
0.7195	Intermediate Similarity	NPD4137	Phase 3
0.7191	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD6942	Approved
0.7176	Intermediate Similarity	NPD7339	Approved
0.7158	Intermediate Similarity	NPD4202	Approved
0.7157	Intermediate Similarity	NPD5697	Approved
0.7126	Intermediate Similarity	NPD6114	Approved
0.7126	Intermediate Similarity	NPD6118	Approved
0.7126	Intermediate Similarity	NPD6115	Approved
0.7126	Intermediate Similarity	NPD6697	Approved
0.7115	Intermediate Similarity	NPD7290	Approved
0.7115	Intermediate Similarity	NPD6883	Approved
0.7115	Intermediate Similarity	NPD7102	Approved
0.7113	Intermediate Similarity	NPD7614	Phase 1
0.7113	Intermediate Similarity	NPD4697	Phase 3
0.7108	Intermediate Similarity	NPD4691	Approved
0.7087	Intermediate Similarity	NPD6011	Approved
0.7073	Intermediate Similarity	NPD3621	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD5360	Phase 3
0.7071	Intermediate Similarity	NPD4696	Approved
0.7071	Intermediate Similarity	NPD5286	Approved
0.7071	Intermediate Similarity	NPD5285	Approved
0.7059	Intermediate Similarity	NPD4058	Approved
0.7059	Intermediate Similarity	NPD5733	Approved
0.7059	Intermediate Similarity	NPD4687	Approved
0.7048	Intermediate Similarity	NPD6869	Approved
0.7048	Intermediate Similarity	NPD6650	Approved
0.7048	Intermediate Similarity	NPD6847	Approved
0.7048	Intermediate Similarity	NPD6649	Approved
0.7048	Intermediate Similarity	NPD8130	Phase 1
0.7048	Intermediate Similarity	NPD6617	Approved
0.7041	Intermediate Similarity	NPD4755	Approved
0.703	Intermediate Similarity	NPD6052	Approved
0.7019	Intermediate Similarity	NPD6012	Approved
0.7019	Intermediate Similarity	NPD6373	Approved
0.7019	Intermediate Similarity	NPD6372	Approved
0.7019	Intermediate Similarity	NPD6013	Approved
0.7019	Intermediate Similarity	NPD6014	Approved
0.7	Intermediate Similarity	NPD5223	Approved
0.699	Remote Similarity	NPD5701	Approved
0.6989	Remote Similarity	NPD3573	Approved
0.6981	Remote Similarity	NPD8297	Approved
0.6981	Remote Similarity	NPD6882	Approved
0.6977	Remote Similarity	NPD5275	Approved
0.6977	Remote Similarity	NPD4190	Phase 3
0.6947	Remote Similarity	NPD4096	Approved
0.6931	Remote Similarity	NPD5226	Approved
0.6931	Remote Similarity	NPD5091	Approved
0.6931	Remote Similarity	NPD4633	Approved
0.6931	Remote Similarity	NPD5211	Phase 2
0.6931	Remote Similarity	NPD5224	Approved
0.6931	Remote Similarity	NPD5225	Approved
0.6915	Remote Similarity	NPD4518	Approved
0.6907	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD7900	Approved
0.6905	Remote Similarity	NPD4789	Approved
0.69	Remote Similarity	NPD4700	Approved
0.6897	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7637	Suspended
0.6875	Remote Similarity	NPD6411	Approved
0.6863	Remote Similarity	NPD5175	Approved
0.6863	Remote Similarity	NPD5174	Approved
0.686	Remote Similarity	NPD6926	Approved
0.686	Remote Similarity	NPD6924	Approved
0.6842	Remote Similarity	NPD6051	Approved
0.6837	Remote Similarity	NPD5654	Approved
0.6827	Remote Similarity	NPD6614	Approved
0.6824	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD5276	Approved
0.6824	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD5133	Approved
0.6796	Remote Similarity	NPD5141	Approved
0.6789	Remote Similarity	NPD6868	Approved
0.6782	Remote Similarity	NPD3702	Approved
0.6778	Remote Similarity	NPD5368	Approved
0.6759	Remote Similarity	NPD4632	Approved
0.6739	Remote Similarity	NPD5332	Approved
0.6739	Remote Similarity	NPD5331	Approved
0.6731	Remote Similarity	NPD6008	Approved
0.6727	Remote Similarity	NPD7115	Discovery
0.6707	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD7144	Approved
0.6706	Remote Similarity	NPD7143	Approved
0.6706	Remote Similarity	NPD4244	Approved
0.6706	Remote Similarity	NPD4245	Approved
0.6705	Remote Similarity	NPD6933	Approved
0.6703	Remote Similarity	NPD4790	Discontinued
0.6703	Remote Similarity	NPD5369	Approved
0.6703	Remote Similarity	NPD857	Phase 3
0.67	Remote Similarity	NPD5959	Approved
0.6699	Remote Similarity	NPD4754	Approved
0.6667	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6335	Approved
0.6667	Remote Similarity	NPD6412	Phase 2
0.6667	Remote Similarity	NPD6101	Approved
0.663	Remote Similarity	NPD4269	Approved
0.663	Remote Similarity	NPD4270	Approved
0.663	Remote Similarity	NPD6435	Approved
0.6628	Remote Similarity	NPD7152	Approved
0.6628	Remote Similarity	NPD7151	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