NPASS Compound

Structure

NPC472282 OpenBabel07101718322D 42 47 0 0 1 0 0 0 0 0999 V2000 1.9207 2.0218 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6290 0.0862 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6813 -3.0919 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1707 -2.2443 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5429 -1.4681 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1723 -3.1554 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3299 -5.8254 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6860 1.4116 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8476 -2.4469 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4928 -1.9522 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6953 -1.9575 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4502 -2.1557 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8476 0.4894 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2847 -0.5807 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5401 0.4437 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3905 -0.9788 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.9575 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.8476 -0.4894 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6953 0.9788 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6953 -0.9788 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7145 -3.6371 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5686 -2.6693 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6953 -1.9575 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5429 -0.4894 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.2483 -1.4919 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8476 -0.4894 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3053 -0.1665 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9492 -4.2474 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1919 -2.2443 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6953 -0.9788 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8476 -2.4469 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -0.9788 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6953 1.9575 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6256 -3.9947 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3905 -2.9363 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2164 0.1911 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0381 -3.8898 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0951 -5.2152 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9396 -1.3080 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5429 0.4894 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1594 -1.1343 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 8 1 0 0 0 0 3 29 1 0 0 0 0 4 29 1 0 0 0 0 7 38 1 0 0 0 0 8 15 1 0 0 0 0 9 11 1 0 0 0 0 9 17 1 0 0 0 0 10 12 2 0 0 0 0 10 16 1 0 0 0 0 11 30 1 0 0 0 0 12 39 1 0 0 0 0 13 18 1 0 0 0 0 13 19 1 0 0 0 0 14 16 2 0 0 0 0 14 39 1 0 0 0 0 15 2 1 1 0 0 0 15 27 1 0 0 0 0 16 24 1 0 0 0 0 17 31 1 0 0 0 0 17 32 1 0 0 0 0 18 30 1 1 0 0 0 18 32 1 0 0 0 0 19 33 2 0 0 0 0 19 40 1 0 0 0 0 20 23 1 1 0 0 0 20 25 1 0 0 0 0 20 26 1 0 0 0 0 21 22 1 0 0 0 0 21 28 1 0 0 0 0 21 34 1 1 0 0 0 22 29 1 0 0 0 0 22 31 1 6 0 0 0 23 31 1 0 0 0 0 23 35 2 0 0 0 0 24 30 1 6 0 0 0 24 40 1 0 0 0 0 25 29 1 0 0 0 0 25 41 1 1 0 0 0 26 32 1 6 0 0 0 26 42 1 0 0 0 0 27 36 2 0 0 0 0 27 41 1 0 0 0 0 28 37 2 0 0 0 0 28 38 1 0 0 0 0 30 5 1 6 0 0 0 31 6 1 6 0 0 0 32 42 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	586.28
Volume:	582.773
LogP:	3.417
LogD:	1.429
LogS:	-3.626
# Rotatable Bonds:	8
TPSA:	141.87
# H-Bond Aceptor:	10
# H-Bond Donor:	1
# Rings:	6
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.285
Synthetic Accessibility Score:	6.865
Fsp3:	0.75
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.307
MDCK Permeability:	3.398659828235395e-05
Pgp-inhibitor:	0.996
Pgp-substrate:	0.276
Human Intestinal Absorption (HIA):	0.018
20% Bioavailability (F20%):	0.011
30% Bioavailability (F30%):	0.432

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.036
Plasma Protein Binding (PPB):	91.23283386230469%
Volume Distribution (VD):	2.054
Pgp-substrate:	9.290580749511719%

ADMET: Metabolism

CYP1A2-inhibitor:	0.005
CYP1A2-substrate:	0.248
CYP2C19-inhibitor:	0.027
CYP2C19-substrate:	0.406
CYP2C9-inhibitor:	0.302
CYP2C9-substrate:	0.025
CYP2D6-inhibitor:	0.012
CYP2D6-substrate:	0.104
CYP3A4-inhibitor:	0.731
CYP3A4-substrate:	0.539

ADMET: Excretion

Clearance (CL):	7.778
Half-life (T1/2):	0.453

ADMET: Toxicity

hERG Blockers:	0.321
Human Hepatotoxicity (H-HT):	0.981
Drug-inuced Liver Injury (DILI):	0.929
AMES Toxicity:	0.018
Rat Oral Acute Toxicity:	0.952
Maximum Recommended Daily Dose:	0.915
Skin Sensitization:	0.104
Carcinogencity:	0.03
Eye Corrosion:	0.008
Eye Irritation:	0.021
Respiratory Toxicity:	0.982

Download Data

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

Natural Product: NPC472282

Natural Product ID:	NPC472282
*Common Name:**	FCMCCFULNAGOLE-GUMQSGBDSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	FCMCCFULNAGOLE-GUMQSGBDSA-N
Standard InCHI:	InChI=1S/C32H42O10/c1-8-15(2)27(36)41-25-20-23(35)31(6,22(29(25,3)4)21(34)28(37)38-7)17-9-11-30(5)18(32(17)26(20)42-32)13-19(33)40-24(30)16-10-12-39-14-16/h10,12,14-15,17-18,20-22,24-26,34H,8-9,11,13H2,1-7H3/t15-,17?,18+,20-,21+,22-,24-,25+,26+,30+,31+,32+/m0/s1
SMILES:	COC(=O)[C@@H]([C@H]1C(C)(C)[C@H](OC(=O)[C@H](CC)C)[C@@H]2C(=O)[C@]1(C)C1CC[C@@]3([C@H]([C@]41[C@@H]2O4)CC(=O)O[C@H]3c1ccoc1)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3357580
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids [CHEMONTID:0002380] Limonoids

*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
NPO3136	Swietenia macrophylla	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10579863]
NPO3136	Swietenia macrophylla	Species	Meliaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[25330401]
NPO3136	Swietenia macrophylla	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
EC50	1
Others	2

Activity Type	# Activity
Organism	1
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT194	Organism	Dengue virus 2	Dengue virus 2	EC50	=	7200.0	nM	PMID[569151]
NPT27	Others	Unspecified		CC50	>	200000.0	nM	PMID[569151]
NPT2	Others	Unspecified		Ratio CC50/EC50	>	27.7	n.a.	PMID[569151]

☑ 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 NPC472282 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	376
0.1-0.2	1476
0.2-0.3	3311
0.3-0.4	5641
0.4-0.5	10057
0.5-0.6	10326
0.6-0.7	9015
0.7-0.8	2083
0.8-0.85	247
0.85-0.9	83
0.9-0.95	66
0.95-1	16

Similarity Score	Similarity Level	Natural Product ID
0.9809	High Similarity	NPC160651
0.9684	High Similarity	NPC471397
0.9682	High Similarity	NPC470875
0.9679	High Similarity	NPC477405
0.962	High Similarity	NPC173516
0.9618	High Similarity	NPC469849
0.9618	High Similarity	NPC476856
0.9618	High Similarity	NPC276551
0.9618	High Similarity	NPC476858
0.9618	High Similarity	NPC476857
0.9615	High Similarity	NPC69028
0.9615	High Similarity	NPC263432
0.9554	High Similarity	NPC134254
0.9554	High Similarity	NPC469338
0.9554	High Similarity	NPC39986
0.9554	High Similarity	NPC292389
0.9554	High Similarity	NPC302369
0.9551	High Similarity	NPC335761
0.9551	High Similarity	NPC25255
0.9497	High Similarity	NPC476853
0.9497	High Similarity	NPC476861
0.9497	High Similarity	NPC476850
0.9494	High Similarity	NPC470940
0.9494	High Similarity	NPC123088
0.949	High Similarity	NPC193798
0.949	High Similarity	NPC470939
0.949	High Similarity	NPC329938
0.949	High Similarity	NPC5079
0.9437	High Similarity	NPC271235
0.9434	High Similarity	NPC23387
0.943	High Similarity	NPC51568
0.943	High Similarity	NPC234660
0.9427	High Similarity	NPC472653
0.9427	High Similarity	NPC477402
0.9375	High Similarity	NPC472775
0.9375	High Similarity	NPC472774
0.9371	High Similarity	NPC476860
0.9359	High Similarity	NPC107646
0.9317	High Similarity	NPC472652
0.9308	High Similarity	NPC476197
0.9308	High Similarity	NPC472773
0.9304	High Similarity	NPC475381
0.9299	High Similarity	NPC472283
0.9299	High Similarity	NPC286722
0.9295	High Similarity	NPC469850
0.9295	High Similarity	NPC469336
0.9255	High Similarity	NPC472651
0.925	High Similarity	NPC271657
0.9245	High Similarity	NPC472771
0.9245	High Similarity	NPC82851
0.9245	High Similarity	NPC117986
0.9245	High Similarity	NPC290400
0.9245	High Similarity	NPC96443
0.9241	High Similarity	NPC475295
0.9241	High Similarity	NPC477403
0.9241	High Similarity	NPC237155
0.9241	High Similarity	NPC473473
0.9236	High Similarity	NPC60973
0.9236	High Similarity	NPC209364
0.9231	High Similarity	NPC178932
0.9187	High Similarity	NPC469846
0.9182	High Similarity	NPC305016
0.9177	High Similarity	NPC249021
0.9177	High Similarity	NPC173544
0.9177	High Similarity	NPC472772
0.9177	High Similarity	NPC45101
0.9172	High Similarity	NPC281258
0.9172	High Similarity	NPC264943
0.9136	High Similarity	NPC473766
0.9136	High Similarity	NPC473753
0.9125	High Similarity	NPC18347
0.9125	High Similarity	NPC149896
0.9125	High Similarity	NPC200782
0.9119	High Similarity	NPC475967
0.9114	High Similarity	NPC126723
0.9114	High Similarity	NPC469485
0.9114	High Similarity	NPC263265
0.9074	High Similarity	NPC475779
0.9057	High Similarity	NPC299038
0.9057	High Similarity	NPC187149
0.9057	High Similarity	NPC167142
0.9051	High Similarity	NPC44675
0.9051	High Similarity	NPC214541
0.9045	High Similarity	NPC469503
0.9045	High Similarity	NPC75906
0.9038	High Similarity	NPC196864
0.9038	High Similarity	NPC159927
0.9038	High Similarity	NPC469335
0.9038	High Similarity	NPC477404
0.9024	High Similarity	NPC82602
0.9024	High Similarity	NPC470995
0.9006	High Similarity	NPC207978
0.9	High Similarity	NPC307383
0.8987	High Similarity	NPC282445
0.8957	High Similarity	NPC121995
0.8944	High Similarity	NPC191828
0.8944	High Similarity	NPC470789
0.8941	High Similarity	NPC105395
0.8938	High Similarity	NPC36655
0.8938	High Similarity	NPC261597
0.8931	High Similarity	NPC476262
0.8924	High Similarity	NPC476201
0.8909	High Similarity	NPC302392
0.8896	High Similarity	NPC470182
0.8889	High Similarity	NPC18986
0.8889	High Similarity	NPC188649
0.8889	High Similarity	NPC211777
0.8868	High Similarity	NPC57998
0.8862	High Similarity	NPC471437
0.8861	High Similarity	NPC18135
0.8855	High Similarity	NPC160818
0.8855	High Similarity	NPC169299
0.8841	High Similarity	NPC97574
0.8841	High Similarity	NPC93172
0.8834	High Similarity	NPC288602
0.8834	High Similarity	NPC663
0.8834	High Similarity	NPC419
0.8834	High Similarity	NPC198047
0.8834	High Similarity	NPC88841
0.8834	High Similarity	NPC224394
0.883	High Similarity	NPC242068
0.883	High Similarity	NPC247563
0.8827	High Similarity	NPC287559
0.8812	High Similarity	NPC35000
0.881	High Similarity	NPC262386
0.8805	High Similarity	NPC44577
0.8802	High Similarity	NPC469848
0.8797	High Similarity	NPC476122
0.8797	High Similarity	NPC46551
0.8788	High Similarity	NPC100333
0.8782	High Similarity	NPC262198
0.8773	High Similarity	NPC68848
0.8765	High Similarity	NPC474611
0.8765	High Similarity	NPC473368
0.8765	High Similarity	NPC262872
0.8757	High Similarity	NPC478177
0.875	High Similarity	NPC94763
0.875	High Similarity	NPC30222
0.8743	High Similarity	NPC159232
0.8743	High Similarity	NPC285227
0.8735	High Similarity	NPC472766
0.8735	High Similarity	NPC472765
0.8735	High Similarity	NPC296558
0.8734	High Similarity	NPC125182
0.8734	High Similarity	NPC69647
0.8727	High Similarity	NPC472141
0.8726	High Similarity	NPC221809
0.872	High Similarity	NPC472139
0.8718	High Similarity	NPC41182
0.8704	High Similarity	NPC472777
0.8704	High Similarity	NPC472778
0.8704	High Similarity	NPC88007
0.8704	High Similarity	NPC472776
0.8704	High Similarity	NPC194499
0.8696	High Similarity	NPC92979
0.8688	High Similarity	NPC268905
0.8683	High Similarity	NPC472659
0.8675	High Similarity	NPC472764
0.8675	High Similarity	NPC270312
0.8659	High Similarity	NPC197596
0.8659	High Similarity	NPC471166
0.8659	High Similarity	NPC472767
0.8659	High Similarity	NPC471167
0.8659	High Similarity	NPC470792
0.8654	High Similarity	NPC476944
0.865	High Similarity	NPC475226
0.8642	High Similarity	NPC41880
0.8639	High Similarity	NPC471632
0.8639	High Similarity	NPC236004
0.8634	High Similarity	NPC302054
0.8634	High Similarity	NPC253201
0.8616	High Similarity	NPC472654
0.8616	High Similarity	NPC195325
0.8614	High Similarity	NPC149945
0.8614	High Similarity	NPC478178
0.8608	High Similarity	NPC470941
0.8608	High Similarity	NPC255414
0.8606	High Similarity	NPC285567
0.8606	High Similarity	NPC283209
0.859	High Similarity	NPC243577
0.8589	High Similarity	NPC197137
0.8589	High Similarity	NPC195954
0.858	High Similarity	NPC75310
0.8571	High Similarity	NPC147168
0.8571	High Similarity	NPC294511
0.8571	High Similarity	NPC472672
0.8571	High Similarity	NPC121615
0.8563	High Similarity	NPC476224
0.8554	High Similarity	NPC146991
0.8554	High Similarity	NPC56358
0.8547	High Similarity	NPC470938
0.8545	High Similarity	NPC79571
0.8538	High Similarity	NPC472665
0.8537	High Similarity	NPC140952
0.8535	High Similarity	NPC137295
0.8535	High Similarity	NPC86935
0.8535	High Similarity	NPC142113
0.8526	High Similarity	NPC121158
0.8519	High Similarity	NPC114880
0.8512	High Similarity	NPC242334

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 NPC472282 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	315
0.1-0.2	1053
0.2-0.3	2253
0.3-0.4	2639
0.4-0.5	1811
0.5-0.6	792
0.6-0.7	254
0.7-0.8	31
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8555	High Similarity	NPD8434	Phase 2
0.8466	Intermediate Similarity	NPD5761	Phase 2
0.8466	Intermediate Similarity	NPD5760	Phase 2
0.8047	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7753	Intermediate Similarity	NPD6764	Approved
0.7753	Intermediate Similarity	NPD6765	Approved
0.7602	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD6785	Approved
0.7582	Intermediate Similarity	NPD6784	Approved
0.7572	Intermediate Similarity	NPD7075	Discontinued
0.7568	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7819	Suspended
0.7486	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD6559	Discontinued
0.7457	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7427	Intermediate Similarity	NPD6599	Discontinued
0.741	Intermediate Similarity	NPD4628	Phase 3
0.7384	Intermediate Similarity	NPD7411	Suspended
0.7377	Intermediate Similarity	NPD8313	Approved
0.7377	Intermediate Similarity	NPD8312	Approved
0.7351	Intermediate Similarity	NPD8150	Discontinued
0.735	Intermediate Similarity	NPD8404	Phase 2
0.7341	Intermediate Similarity	NPD6801	Discontinued
0.7293	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD3749	Approved
0.7267	Intermediate Similarity	NPD3226	Approved
0.7257	Intermediate Similarity	NPD5402	Approved
0.7247	Intermediate Similarity	NPD8127	Discontinued
0.7238	Intermediate Similarity	NPD7799	Discontinued
0.7238	Intermediate Similarity	NPD3751	Discontinued
0.7235	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD4380	Phase 2
0.7222	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD6166	Phase 2
0.7222	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD3787	Discontinued
0.7198	Intermediate Similarity	NPD5844	Phase 1
0.7191	Intermediate Similarity	NPD5494	Approved
0.7176	Intermediate Similarity	NPD6799	Approved
0.7175	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD3817	Phase 2
0.7151	Intermediate Similarity	NPD5403	Approved
0.7143	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD5401	Approved
0.7126	Intermediate Similarity	NPD1471	Phase 3
0.7118	Intermediate Similarity	NPD7236	Approved
0.7093	Intermediate Similarity	NPD6273	Approved
0.7092	Intermediate Similarity	NPD7435	Discontinued
0.7088	Intermediate Similarity	NPD7473	Discontinued
0.7081	Intermediate Similarity	NPD7685	Pre-registration
0.7062	Intermediate Similarity	NPD8285	Discontinued
0.7056	Intermediate Similarity	NPD1247	Approved
0.7052	Intermediate Similarity	NPD920	Approved
0.7049	Intermediate Similarity	NPD3818	Discontinued
0.7043	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD7808	Phase 3
0.7039	Intermediate Similarity	NPD919	Approved
0.7024	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD3882	Suspended
0.7011	Intermediate Similarity	NPD7239	Suspended
0.7006	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD7251	Discontinued
0.6973	Remote Similarity	NPD7074	Phase 3
0.6971	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD7458	Discontinued
0.6968	Remote Similarity	NPD8407	Phase 2
0.6965	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6965	Remote Similarity	NPD7874	Approved
0.6961	Remote Similarity	NPD6959	Discontinued
0.6957	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD1934	Approved
0.6939	Remote Similarity	NPD6777	Approved
0.6939	Remote Similarity	NPD6776	Approved
0.6939	Remote Similarity	NPD6782	Approved
0.6939	Remote Similarity	NPD6780	Approved
0.6939	Remote Similarity	NPD6781	Approved
0.6939	Remote Similarity	NPD6779	Approved
0.6939	Remote Similarity	NPD6778	Approved
0.6936	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD6797	Phase 2
0.6927	Remote Similarity	NPD7768	Phase 2
0.6923	Remote Similarity	NPD6232	Discontinued
0.6923	Remote Similarity	NPD2346	Discontinued
0.6919	Remote Similarity	NPD7696	Phase 3
0.6919	Remote Similarity	NPD7698	Approved
0.6919	Remote Similarity	NPD7054	Approved
0.6919	Remote Similarity	NPD7697	Approved
0.6911	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.691	Remote Similarity	NPD8455	Phase 2
0.6901	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6898	Remote Similarity	NPD8368	Discontinued
0.6884	Remote Similarity	NPD8319	Approved
0.6884	Remote Similarity	NPD7871	Phase 2
0.6884	Remote Similarity	NPD8320	Phase 1
0.6884	Remote Similarity	NPD7870	Phase 2
0.6882	Remote Similarity	NPD7472	Approved
0.6867	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD7701	Phase 2
0.6865	Remote Similarity	NPD7228	Approved
0.6854	Remote Similarity	NPD37	Approved
0.6847	Remote Similarity	NPD7801	Approved
0.6839	Remote Similarity	NPD2534	Approved
0.6839	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD2532	Approved
0.6839	Remote Similarity	NPD2533	Approved
0.6833	Remote Similarity	NPD4965	Approved
0.6833	Remote Similarity	NPD4967	Phase 2
0.6833	Remote Similarity	NPD4966	Approved
0.6826	Remote Similarity	NPD6355	Discontinued
0.6823	Remote Similarity	NPD8435	Approved
0.6823	Remote Similarity	NPD8360	Approved
0.6823	Remote Similarity	NPD8361	Approved
0.6821	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD2799	Discontinued
0.6794	Remote Similarity	NPD7907	Approved
0.6793	Remote Similarity	NPD3926	Phase 2
0.6793	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD1549	Phase 2
0.6779	Remote Similarity	NPD4111	Phase 1
0.6776	Remote Similarity	NPD7199	Phase 2
0.6765	Remote Similarity	NPD6100	Approved
0.6765	Remote Similarity	NPD2796	Approved
0.6765	Remote Similarity	NPD7783	Phase 2
0.6765	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD6099	Approved
0.6758	Remote Similarity	NPD6234	Discontinued
0.6751	Remote Similarity	NPD7700	Phase 2
0.6751	Remote Similarity	NPD7699	Phase 2
0.6746	Remote Similarity	NPD7097	Phase 1
0.673	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6725	Remote Similarity	NPD5762	Approved
0.6725	Remote Similarity	NPD5763	Approved
0.6725	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6725	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6722	Remote Similarity	NPD1465	Phase 2
0.6722	Remote Similarity	NPD2801	Approved
0.672	Remote Similarity	NPD7240	Approved
0.6706	Remote Similarity	NPD7033	Discontinued
0.6705	Remote Similarity	NPD3750	Approved
0.6699	Remote Similarity	NPD4665	Approved
0.6687	Remote Similarity	NPD7095	Approved
0.6684	Remote Similarity	NPD6535	Approved
0.6684	Remote Similarity	NPD6534	Approved
0.6667	Remote Similarity	NPD7497	Discontinued
0.6667	Remote Similarity	NPD8151	Discontinued
0.6667	Remote Similarity	NPD1551	Phase 2
0.6667	Remote Similarity	NPD6190	Approved
0.6667	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD7229	Phase 3
0.6648	Remote Similarity	NPD7057	Phase 3
0.6648	Remote Similarity	NPD7058	Phase 2
0.6647	Remote Similarity	NPD3268	Approved
0.6647	Remote Similarity	NPD2800	Approved
0.6647	Remote Similarity	NPD1243	Approved
0.6647	Remote Similarity	NPD2313	Discontinued
0.6647	Remote Similarity	NPD6798	Discontinued
0.6635	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6628	Remote Similarity	NPD2344	Approved
0.6627	Remote Similarity	NPD6832	Phase 2
0.6617	Remote Similarity	NPD3057	Approved
0.6617	Remote Similarity	NPD6823	Phase 2
0.6616	Remote Similarity	NPD8485	Approved
0.661	Remote Similarity	NPD1512	Approved
0.6609	Remote Similarity	NPD8166	Discontinued
0.6609	Remote Similarity	NPD7003	Approved
0.6608	Remote Similarity	NPD3748	Approved
0.6607	Remote Similarity	NPD6233	Phase 2
0.6607	Remote Similarity	NPD8032	Phase 2
0.66	Remote Similarity	NPD4107	Approved
0.659	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD7930	Approved
0.657	Remote Similarity	NPD2935	Discontinued
0.6559	Remote Similarity	NPD6808	Phase 2
0.6548	Remote Similarity	NPD3764	Approved
0.6548	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD2972	Approved
0.6535	Remote Similarity	NPD3533	Approved
0.652	Remote Similarity	NPD7999	Approved
0.6517	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD4580	Approved
0.6512	Remote Similarity	NPD1510	Phase 2
0.6497	Remote Similarity	NPD1511	Approved
0.6497	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6494	Remote Similarity	NPD2424	Discontinued
0.6489	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD2403	Approved
0.6489	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6485	Remote Similarity	NPD4482	Phase 3
0.648	Remote Similarity	NPD4287	Approved
0.6477	Remote Similarity	NPD2354	Approved
0.6477	Remote Similarity	NPD2309	Approved
0.6477	Remote Similarity	NPD3887	Approved
0.6471	Remote Similarity	NPD5711	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