NPASS Compound

Structure

NPC149945 OpenBabel07101718272D 39 43 0 0 1 0 0 0 0 0999 V2000 -0.9176 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3668 1.4739 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1348 2.0101 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6348 1.1441 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6158 0.2045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1349 0.3508 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7864 4.4792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6245 0.9000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6245 0.9000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0543 2.4792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0543 0.1388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4623 -0.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1245 -0.6389 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6213 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0824 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3668 0.4739 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3155 -0.0511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0543 1.4792 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6348 0.4739 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4739 0.4739 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.9204 2.9792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2054 -1.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3644 -0.3601 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6348 1.1441 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6213 0.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4739 1.1441 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6702 1.6180 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6702 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.2328 -0.0261 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7864 2.4792 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9975 -2.6254 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3827 2.5419 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9350 2.5824 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9204 3.9792 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9335 -0.0511 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5008 -0.0261 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1565 -1.3383 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 15 2 0 0 0 0 2 16 1 0 0 0 0 3 25 1 0 0 0 0 4 25 1 0 0 0 0 5 26 1 0 0 0 0 7 35 1 0 0 0 0 8 9 2 0 0 0 0 8 17 1 0 0 0 0 9 36 1 0 0 0 0 10 18 1 0 0 0 0 10 21 1 0 0 0 0 11 19 1 0 0 0 0 11 20 1 0 0 0 0 12 22 1 0 0 0 0 13 17 2 0 0 0 0 13 36 1 0 0 0 0 14 26 1 0 0 0 0 14 28 1 0 0 0 0 15 28 1 0 0 0 0 15 29 1 0 0 0 0 16 30 2 0 0 0 0 16 37 1 0 0 0 0 17 23 1 0 0 0 0 18 25 1 0 0 0 0 18 27 1 6 0 0 0 19 25 1 0 0 0 0 19 37 1 1 0 0 0 20 27 1 1 0 0 0 20 39 1 0 0 0 0 21 31 2 0 0 0 0 21 35 1 0 0 0 0 22 32 2 0 0 0 0 22 38 1 0 0 0 0 23 26 1 6 0 0 0 23 38 1 0 0 0 0 24 27 1 0 0 0 0 24 28 1 0 0 0 0 24 33 2 0 0 0 0 26 29 1 6 0 0 0 27 6 1 6 0 0 0 28 34 1 6 0 0 0 29 12 1 6 0 0 0 29 39 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	544.23
Volume:	536.805
LogP:	2.951
LogD:	1.784
LogS:	-4.922
# Rotatable Bonds:	6
TPSA:	138.57
# H-Bond Aceptor:	10
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.341
Synthetic Accessibility Score:	6.463
Fsp3:	0.655
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-5.309
MDCK Permeability:	5.308312756824307e-05
Pgp-inhibitor:	0.992
Pgp-substrate:	0.035
Human Intestinal Absorption (HIA):	0.259
20% Bioavailability (F20%):	0.879
30% Bioavailability (F30%):	0.94

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.925
Plasma Protein Binding (PPB):	67.26030731201172%
Volume Distribution (VD):	1.311
Pgp-substrate:	37.486846923828125%

ADMET: Metabolism

CYP1A2-inhibitor:	0.002
CYP1A2-substrate:	0.136
CYP2C19-inhibitor:	0.148
CYP2C19-substrate:	0.38
CYP2C9-inhibitor:	0.461
CYP2C9-substrate:	0.017
CYP2D6-inhibitor:	0.01
CYP2D6-substrate:	0.054
CYP3A4-inhibitor:	0.92
CYP3A4-substrate:	0.91

ADMET: Excretion

Clearance (CL):	2.95
Half-life (T1/2):	0.4

ADMET: Toxicity

hERG Blockers:	0.01
Human Hepatotoxicity (H-HT):	0.492
Drug-inuced Liver Injury (DILI):	0.706
AMES Toxicity:	0.177
Rat Oral Acute Toxicity:	0.976
Maximum Recommended Daily Dose:	0.977
Skin Sensitization:	0.095
Carcinogencity:	0.734
Eye Corrosion:	0.231
Eye Irritation:	0.108
Respiratory Toxicity:	0.957

Download Data

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

Natural Product: NPC149945

Natural Product ID:	NPC149945
*Common Name:**	Cipatrijugin B
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	GOEQVXYKRUHLMM-IZZXIUOXSA-N
Standard InCHI:	InChI=1S/C29H36O10/c1-15-28(34)14-26(5)23(17-8-9-36-13-17)38-22(32)12-29(15,26)39-20-11-19(37-16(2)30)25(3,4)18(10-21(31)35-7)27(20,6)24(28)33/h8-9,13,18-20,23,34H,1,10-12,14H2,2-7H3/t18-,19+,20-,23-,26-,27+,28+,29-/m0/s1
SMILES:	C=C1[C@@]2(C[C@@]3(C)[C@H](c4ccoc4)OC(=O)C[C@]13O[C@H]1C[C@H](C(C)(C)[C@H](CC(=O)OC)[C@@]1(C)C2=O)OC(=O)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL400181
PubChem CID:	23626011
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0001986] Tricarboxylic acids and derivatives

*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
NPO4584	Cipadessa cinerascens	Species	Meliaceae	Eukaryota	leaves	n.a.	n.a.	PMID[17655260]
NPO4584	Cipadessa cinerascens	Species	Meliaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[19296669]
NPO4584	Cipadessa cinerascens	Species	Meliaceae	Eukaryota	leaves	Longlin County of Guangxi Province, China	2012-JUL	PMID[25970729]
NPO4584	Cipadessa cinerascens	Species	Meliaceae	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
ED50	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	ED50	>	5.0	ug ml-1	PMID[507067]
NPT111	Cell Line	K562	Homo sapiens	ED50	>	5.0	ug ml-1	PMID[507067]

☑ 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 NPC149945 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	356
0.1-0.2	1501
0.2-0.3	3216
0.3-0.4	6023
0.4-0.5	11218
0.5-0.6	10088
0.6-0.7	8833
0.7-0.8	1129
0.8-0.85	253
0.85-0.9	67
0.9-0.95	3
0.95-1	10

Similarity Score	Similarity Level	Natural Product ID
0.9677	High Similarity	NPC6326
0.9677	High Similarity	NPC472767
0.961	High Similarity	NPC195131
0.9557	High Similarity	NPC472764
0.9545	High Similarity	NPC204663
0.9497	High Similarity	NPC472766
0.9497	High Similarity	NPC472765
0.9434	High Similarity	NPC476224
0.9245	High Similarity	NPC165218
0.9152	High Similarity	NPC478177
0.9146	High Similarity	NPC471632
0.9146	High Similarity	NPC471437
0.913	High Similarity	NPC478178
0.9125	High Similarity	NPC663
0.9125	High Similarity	NPC224394
0.9114	High Similarity	NPC472772
0.903	High Similarity	NPC236004
0.903	High Similarity	NPC94763
0.9024	High Similarity	NPC285227
0.9012	High Similarity	NPC214600
0.8994	High Similarity	NPC249021
0.8963	High Similarity	NPC472659
0.8957	High Similarity	NPC472775
0.8957	High Similarity	NPC472774
0.8957	High Similarity	NPC478179
0.8944	High Similarity	NPC472771
0.8938	High Similarity	NPC477403
0.8889	High Similarity	NPC472773
0.8882	High Similarity	NPC477402
0.8854	High Similarity	NPC156189
0.8841	High Similarity	NPC476853
0.8834	High Similarity	NPC470940
0.8827	High Similarity	NPC197596
0.8827	High Similarity	NPC329938
0.8827	High Similarity	NPC193798
0.8827	High Similarity	NPC82851
0.8805	High Similarity	NPC282445
0.8802	High Similarity	NPC469576
0.8795	High Similarity	NPC159232
0.8788	High Similarity	NPC327922
0.8773	High Similarity	NPC472669
0.8773	High Similarity	NPC292389
0.8773	High Similarity	NPC477405
0.8773	High Similarity	NPC469338
0.8765	High Similarity	NPC470789
0.8765	High Similarity	NPC25255
0.8758	High Similarity	NPC167142
0.8758	High Similarity	NPC45101
0.8758	High Similarity	NPC36655
0.8758	High Similarity	NPC261597
0.875	High Similarity	NPC264943
0.875	High Similarity	NPC469633
0.875	High Similarity	NPC469336
0.8727	High Similarity	NPC173516
0.8727	High Similarity	NPC476861
0.8727	High Similarity	NPC476850
0.872	High Similarity	NPC476857
0.872	High Similarity	NPC476860
0.872	High Similarity	NPC469849
0.872	High Similarity	NPC476856
0.872	High Similarity	NPC123088
0.872	High Similarity	NPC276551
0.872	High Similarity	NPC476858
0.8712	High Similarity	NPC472668
0.8712	High Similarity	NPC69028
0.8712	High Similarity	NPC471166
0.8712	High Similarity	NPC471167
0.8706	High Similarity	NPC470938
0.8704	High Similarity	NPC237155
0.8704	High Similarity	NPC472779
0.8696	High Similarity	NPC469485
0.8688	High Similarity	NPC178932
0.8675	High Similarity	NPC471397
0.8675	High Similarity	NPC160651
0.8671	High Similarity	NPC470791
0.8671	High Similarity	NPC472654
0.8671	High Similarity	NPC470790
0.8667	High Similarity	NPC470875
0.8667	High Similarity	NPC23387
0.8662	High Similarity	NPC470941
0.8659	High Similarity	NPC471168
0.8642	High Similarity	NPC173544
0.8634	High Similarity	NPC214541
0.8634	High Similarity	NPC44675
0.8631	High Similarity	NPC469848
0.8625	High Similarity	NPC75906
0.8625	High Similarity	NPC469503
0.8616	High Similarity	NPC469335
0.8616	High Similarity	NPC477404
0.8616	High Similarity	NPC159927
0.8616	High Similarity	NPC196864
0.8614	High Similarity	NPC472282
0.8614	High Similarity	NPC472651
0.8598	High Similarity	NPC263432
0.8598	High Similarity	NPC470939
0.8589	High Similarity	NPC475967
0.8589	High Similarity	NPC474932
0.8563	High Similarity	NPC472652
0.8562	High Similarity	NPC272590
0.8555	High Similarity	NPC247563
0.8555	High Similarity	NPC105395
0.8555	High Similarity	NPC242068
0.8553	High Similarity	NPC329180
0.8545	High Similarity	NPC302369
0.8545	High Similarity	NPC134254
0.8545	High Similarity	NPC39986
0.8545	High Similarity	NPC419
0.8537	High Similarity	NPC191828
0.8537	High Similarity	NPC472653
0.8528	High Similarity	NPC470118
0.8528	High Similarity	NPC472283
0.8528	High Similarity	NPC187149
0.8519	High Similarity	NPC469850
0.85	High Similarity	NPC476122
0.8494	Intermediate Similarity	NPC261184
0.8485	Intermediate Similarity	NPC5741
0.8485	Intermediate Similarity	NPC5079
0.8485	Intermediate Similarity	NPC200782
0.8481	Intermediate Similarity	NPC262198
0.8481	Intermediate Similarity	NPC346
0.8476	Intermediate Similarity	NPC475226
0.8466	Intermediate Similarity	NPC126723
0.8466	Intermediate Similarity	NPC263265
0.8457	Intermediate Similarity	NPC57998
0.8457	Intermediate Similarity	NPC30222
0.8452	Intermediate Similarity	NPC271235
0.8452	Intermediate Similarity	NPC242334
0.8438	Intermediate Similarity	NPC195325
0.8434	Intermediate Similarity	NPC51568
0.8434	Intermediate Similarity	NPC234660
0.8428	Intermediate Similarity	NPC250228
0.8428	Intermediate Similarity	NPC221809
0.8424	Intermediate Similarity	NPC335761
0.8424	Intermediate Similarity	NPC305016
0.8415	Intermediate Similarity	NPC472776
0.8415	Intermediate Similarity	NPC299038
0.8415	Intermediate Similarity	NPC472778
0.8415	Intermediate Similarity	NPC197137
0.8415	Intermediate Similarity	NPC475066
0.8415	Intermediate Similarity	NPC472777
0.8415	Intermediate Similarity	NPC286722
0.8408	Intermediate Similarity	NPC243577
0.8405	Intermediate Similarity	NPC35000
0.8405	Intermediate Similarity	NPC471175
0.8405	Intermediate Similarity	NPC92979
0.8405	Intermediate Similarity	NPC75310
0.8402	Intermediate Similarity	NPC470995
0.8395	Intermediate Similarity	NPC476201
0.8395	Intermediate Similarity	NPC246164
0.8383	Intermediate Similarity	NPC259943
0.8383	Intermediate Similarity	NPC470182
0.8383	Intermediate Similarity	NPC271657
0.8373	Intermediate Similarity	NPC117986
0.8373	Intermediate Similarity	NPC18347
0.8373	Intermediate Similarity	NPC149896
0.8364	Intermediate Similarity	NPC473473
0.8364	Intermediate Similarity	NPC475295
0.8354	Intermediate Similarity	NPC60973
0.8354	Intermediate Similarity	NPC476944
0.8354	Intermediate Similarity	NPC41880
0.8354	Intermediate Similarity	NPC209364
0.8354	Intermediate Similarity	NPC251865
0.8354	Intermediate Similarity	NPC175964
0.8354	Intermediate Similarity	NPC471169
0.8354	Intermediate Similarity	NPC107646
0.8353	Intermediate Similarity	NPC160818
0.8353	Intermediate Similarity	NPC169299
0.8344	Intermediate Similarity	NPC121158
0.8343	Intermediate Similarity	NPC472673
0.8333	Intermediate Similarity	NPC116717
0.8333	Intermediate Similarity	NPC18135
0.8323	Intermediate Similarity	NPC88841
0.8323	Intermediate Similarity	NPC288602
0.8323	Intermediate Similarity	NPC476197
0.8323	Intermediate Similarity	NPC469846
0.8323	Intermediate Similarity	NPC211625
0.8314	Intermediate Similarity	NPC167340
0.8313	Intermediate Similarity	NPC475381
0.8313	Intermediate Similarity	NPC471174
0.8313	Intermediate Similarity	NPC216755
0.8313	Intermediate Similarity	NPC255414
0.8294	Intermediate Similarity	NPC82602
0.8294	Intermediate Similarity	NPC472650
0.8293	Intermediate Similarity	NPC281258
0.8293	Intermediate Similarity	NPC476262
0.8291	Intermediate Similarity	NPC267632
0.8291	Intermediate Similarity	NPC223415
0.8284	Intermediate Similarity	NPC473753
0.8284	Intermediate Similarity	NPC473766
0.8282	Intermediate Similarity	NPC44577
0.8282	Intermediate Similarity	NPC84063
0.8282	Intermediate Similarity	NPC476939
0.8282	Intermediate Similarity	NPC475777
0.8282	Intermediate Similarity	NPC476940
0.8282	Intermediate Similarity	NPC182427
0.8282	Intermediate Similarity	NPC29695
0.828	Intermediate Similarity	NPC205765
0.8266	Intermediate Similarity	NPC470181
0.8263	Intermediate Similarity	NPC188649
0.8263	Intermediate Similarity	NPC290400

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 NPC149945 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	307
0.1-0.2	1035
0.2-0.3	2258
0.3-0.4	2708
0.4-0.5	1843
0.5-0.6	766
0.6-0.7	216
0.7-0.8	15
0.8-0.85	0
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8868	High Similarity	NPD5760	Phase 2
0.8868	High Similarity	NPD5761	Phase 2
0.7988	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7978	Intermediate Similarity	NPD8434	Phase 2
0.7797	Intermediate Similarity	NPD6764	Approved
0.7797	Intermediate Similarity	NPD6765	Approved
0.7624	Intermediate Similarity	NPD6785	Approved
0.7624	Intermediate Similarity	NPD6784	Approved
0.7341	Intermediate Similarity	NPD7819	Suspended
0.7314	Intermediate Similarity	NPD7075	Discontinued
0.7243	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD7411	Suspended
0.72	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD920	Approved
0.7119	Intermediate Similarity	NPD3749	Approved
0.7076	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD6599	Discontinued
0.7066	Intermediate Similarity	NPD6004	Phase 3
0.7066	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD6005	Phase 3
0.7066	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD6002	Phase 3
0.7059	Intermediate Similarity	NPD7236	Approved
0.7027	Intermediate Similarity	NPD6559	Discontinued
0.7011	Intermediate Similarity	NPD3226	Approved
0.7	Intermediate Similarity	NPD1247	Approved
0.6995	Remote Similarity	NPD7799	Discontinued
0.6989	Remote Similarity	NPD6801	Discontinued
0.6983	Remote Similarity	NPD919	Approved
0.6982	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD2532	Approved
0.6977	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD2534	Approved
0.6977	Remote Similarity	NPD2533	Approved
0.6964	Remote Similarity	NPD1471	Phase 3
0.6964	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD7239	Suspended
0.6946	Remote Similarity	NPD2799	Discontinued
0.6941	Remote Similarity	NPD4628	Phase 3
0.6941	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD6273	Approved
0.6919	Remote Similarity	NPD6799	Approved
0.6882	Remote Similarity	NPD2800	Approved
0.6879	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD8404	Phase 2
0.6875	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD3882	Suspended
0.6854	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6851	Remote Similarity	NPD5494	Approved
0.6845	Remote Similarity	NPD7685	Pre-registration
0.6824	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD1549	Phase 2
0.6816	Remote Similarity	NPD5402	Approved
0.6816	Remote Similarity	NPD3817	Phase 2
0.6784	Remote Similarity	NPD1243	Approved
0.678	Remote Similarity	NPD4380	Phase 2
0.6778	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD7473	Discontinued
0.6748	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.674	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD8127	Discontinued
0.6721	Remote Similarity	NPD6959	Discontinued
0.672	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.672	Remote Similarity	NPD3818	Discontinued
0.6706	Remote Similarity	NPD6100	Approved
0.6706	Remote Similarity	NPD6099	Approved
0.6706	Remote Similarity	NPD1551	Phase 2
0.6706	Remote Similarity	NPD2796	Approved
0.6705	Remote Similarity	NPD5403	Approved
0.6704	Remote Similarity	NPD1934	Approved
0.6703	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD6166	Phase 2
0.6703	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD7768	Phase 2
0.6684	Remote Similarity	NPD5844	Phase 1
0.6667	Remote Similarity	NPD2346	Discontinued
0.6667	Remote Similarity	NPD5763	Approved
0.6667	Remote Similarity	NPD2344	Approved
0.6667	Remote Similarity	NPD5762	Approved
0.6649	Remote Similarity	NPD3926	Phase 2
0.6647	Remote Similarity	NPD7033	Discontinued
0.6647	Remote Similarity	NPD3750	Approved
0.6647	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.663	Remote Similarity	NPD7199	Phase 2
0.6617	Remote Similarity	NPD7497	Discontinued
0.6608	Remote Similarity	NPD2935	Discontinued
0.6597	Remote Similarity	NPD8312	Approved
0.6597	Remote Similarity	NPD8313	Approved
0.6595	Remote Similarity	NPD5710	Approved
0.6595	Remote Similarity	NPD5711	Approved
0.6595	Remote Similarity	NPD6232	Discontinued
0.6593	Remote Similarity	NPD7057	Phase 3
0.6593	Remote Similarity	NPD7058	Phase 2
0.6591	Remote Similarity	NPD5401	Approved
0.6587	Remote Similarity	NPD3268	Approved
0.6587	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.658	Remote Similarity	NPD8150	Discontinued
0.6579	Remote Similarity	NPD7251	Discontinued
0.6568	Remote Similarity	NPD6355	Discontinued
0.6566	Remote Similarity	NPD6832	Phase 2
0.6561	Remote Similarity	NPD7074	Phase 3
0.655	Remote Similarity	NPD1510	Phase 2
0.6545	Remote Similarity	NPD7808	Phase 3
0.6545	Remote Similarity	NPD5647	Approved
0.6543	Remote Similarity	NPD3751	Discontinued
0.6536	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD7435	Discontinued
0.6529	Remote Similarity	NPD6653	Approved
0.6529	Remote Similarity	NPD6651	Approved
0.6526	Remote Similarity	NPD5953	Discontinued
0.6526	Remote Similarity	NPD6797	Phase 2
0.6514	Remote Similarity	NPD2309	Approved
0.6509	Remote Similarity	NPD1240	Approved
0.6508	Remote Similarity	NPD7054	Approved
0.6508	Remote Similarity	NPD7286	Phase 2
0.6505	Remote Similarity	NPD7229	Phase 3
0.6505	Remote Similarity	NPD6808	Phase 2
0.6503	Remote Similarity	NPD4965	Approved
0.6503	Remote Similarity	NPD4966	Approved
0.6503	Remote Similarity	NPD4967	Phase 2
0.6488	Remote Similarity	NPD2313	Discontinued
0.6484	Remote Similarity	NPD2801	Approved
0.6474	Remote Similarity	NPD7472	Approved
0.6461	Remote Similarity	NPD1512	Approved
0.6453	Remote Similarity	NPD3748	Approved
0.6444	Remote Similarity	NPD7458	Discontinued
0.6436	Remote Similarity	NPD2403	Approved
0.6433	Remote Similarity	NPD1607	Approved
0.6432	Remote Similarity	NPD6234	Discontinued
0.6432	Remote Similarity	NPD7907	Approved
0.6429	Remote Similarity	NPD37	Approved
0.6417	Remote Similarity	NPD3787	Discontinued
0.6412	Remote Similarity	NPD4140	Approved
0.6412	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6402	Remote Similarity	NPD1608	Approved
0.6402	Remote Similarity	NPD9717	Approved
0.6393	Remote Similarity	NPD1465	Phase 2
0.6392	Remote Similarity	NPD8407	Phase 2
0.6391	Remote Similarity	NPD3764	Approved
0.6386	Remote Similarity	NPD6778	Approved
0.6386	Remote Similarity	NPD6362	Approved
0.6386	Remote Similarity	NPD6779	Approved
0.6386	Remote Similarity	NPD6777	Approved
0.6386	Remote Similarity	NPD6780	Approved
0.6386	Remote Similarity	NPD6776	Approved
0.6386	Remote Similarity	NPD6782	Approved
0.6386	Remote Similarity	NPD6781	Approved
0.6374	Remote Similarity	NPD447	Suspended
0.6374	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD7696	Phase 3
0.6373	Remote Similarity	NPD7698	Approved
0.6373	Remote Similarity	NPD7697	Approved
0.6368	Remote Similarity	NPD7228	Approved
0.6353	Remote Similarity	NPD8032	Phase 2
0.6353	Remote Similarity	NPD6663	Approved
0.6348	Remote Similarity	NPD1511	Approved
0.6346	Remote Similarity	NPD7874	Approved
0.6346	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6345	Remote Similarity	NPD4287	Approved
0.6341	Remote Similarity	NPD7871	Phase 2
0.6341	Remote Similarity	NPD7870	Phase 2
0.6338	Remote Similarity	NPD4665	Approved
0.6338	Remote Similarity	NPD4111	Phase 1
0.6333	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.633	Remote Similarity	NPD7315	Approved
0.6321	Remote Similarity	NPD8368	Discontinued
0.6319	Remote Similarity	NPD7028	Phase 2
0.6296	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6294	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6287	Remote Similarity	NPD3267	Approved
0.6287	Remote Similarity	NPD2797	Approved
0.6287	Remote Similarity	NPD1203	Approved
0.6287	Remote Similarity	NPD3266	Approved
0.6279	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6279	Remote Similarity	NPD5124	Phase 1
0.6279	Remote Similarity	NPD230	Phase 1
0.6279	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6271	Remote Similarity	NPD7003	Approved
0.6264	Remote Similarity	NPD4308	Phase 3
0.6263	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD8319	Approved
0.6262	Remote Similarity	NPD8320	Phase 1
0.6257	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6256	Remote Similarity	NPD8285	Discontinued
0.625	Remote Similarity	NPD7701	Phase 2
0.6243	Remote Similarity	NPD6353	Approved
0.6238	Remote Similarity	NPD7801	Approved
0.6238	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6236	Remote Similarity	NPD6190	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