NPASS Compound

Structure

NPC475960 OpenBabel07101718312D 22 25 0 0 1 0 0 0 0 0999 V2000 -0.3105 -3.3173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4805 3.0455 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3474 -2.5642 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9705 1.2946 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3707 0.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0242 -1.6179 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9169 0.9714 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.7610 1.0347 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.9019 -0.0285 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9314 -1.3231 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5998 -0.8001 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1264 1.9656 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3368 0.4142 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4775 -0.8462 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9463 -0.3232 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5997 -0.7852 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5029 2.7474 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2924 0.7089 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1152 2.1146 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8777 -1.6463 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2106 -0.4229 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 3 1 0 0 0 0 2 19 1 0 0 0 0 3 6 2 0 0 0 0 4 5 2 0 0 0 0 6 10 1 0 0 0 0 6 11 1 0 0 0 0 7 4 1 6 0 0 0 7 8 1 0 0 0 0 7 9 1 0 0 0 0 8 12 1 6 0 0 0 8 13 1 0 0 0 0 9 14 1 0 0 0 0 9 15 1 6 0 0 0 10 15 1 1 0 0 0 10 20 1 0 0 0 0 11 16 2 0 0 0 0 11 22 1 0 0 0 0 12 17 2 0 0 0 0 12 19 1 0 0 0 0 13 18 1 1 0 0 0 13 21 1 0 0 0 0 14 20 1 6 0 0 0 14 21 1 0 0 0 0 15 5 1 6 0 0 0 15 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	308.09
Volume:	284.756
LogP:	0.55
LogD:	0.314
LogS:	-2.575
# Rotatable Bonds:	2
TPSA:	91.29
# H-Bond Aceptor:	7
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.41
Synthetic Accessibility Score:	5.744
Fsp3:	0.6
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.045
MDCK Permeability:	5.620845331577584e-05
Pgp-inhibitor:	0.066
Pgp-substrate:	0.027
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.398
30% Bioavailability (F30%):	0.815

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.534
Plasma Protein Binding (PPB):	25.05901527404785%
Volume Distribution (VD):	1.4
Pgp-substrate:	70.94282531738281%

ADMET: Metabolism

CYP1A2-inhibitor:	0.024
CYP1A2-substrate:	0.941
CYP2C19-inhibitor:	0.03
CYP2C19-substrate:	0.832
CYP2C9-inhibitor:	0.015
CYP2C9-substrate:	0.021
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.124
CYP3A4-inhibitor:	0.368
CYP3A4-substrate:	0.353

ADMET: Excretion

Clearance (CL):	3.946
Half-life (T1/2):	0.736

ADMET: Toxicity

hERG Blockers:	0.267
Human Hepatotoxicity (H-HT):	0.959
Drug-inuced Liver Injury (DILI):	0.742
AMES Toxicity:	0.933
Rat Oral Acute Toxicity:	0.802
Maximum Recommended Daily Dose:	0.937
Skin Sensitization:	0.295
Carcinogencity:	0.019
Eye Corrosion:	0.004
Eye Irritation:	0.015
Respiratory Toxicity:	0.942

Download Data

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

Natural Product: NPC475960

Natural Product ID:	NPC475960
*Common Name:**	Allamandin
IUPAC Name:	n.a.
Synonyms:	Allamandin
Standard InCHIKey:	UEOKCUGZTJHPBW-FNIPEDCFSA-N
Standard InCHI:	InChI=1S/C15H16O7/c1-3-6-10-15(22-11(6)16)5-4-7-8(12(17)19-2)13(18)21-14(20-10)9(7)15/h3-5,7-10,13-14,18H,1-2H3/b6-3+/t7-,8-,9-,10+,13+,14+,15+/m0/s1
SMILES:	COC(=O)[C@H]1[C@H](O)O[C@@H]2[C@@H]3[C@H]1C=C[C@]13OC(=O)/C(=C/C)/[C@H]1O2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL519742
PubChem CID:	6436806
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones

*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
NPO12734	Plumeria rubra	Species	Apocynaceae	Eukaryota	bark	Indonesia	n.a.	PMID[1965200]
NPO40011	Allamanda schottii	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[3379414]
NPO12734	Plumeria rubra	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12734	Plumeria rubra	Species	Apocynaceae	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	8
Others	3

Activity Type	# Activity
Cell Line	4
NON-MOLECULAR	5
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	T/C	=	145.0	%	PMID[494608]
NPT453	Cell Line	HT-1080	Homo sapiens	ED50	=	0.8	ug ml-1	PMID[494609]
NPT91	Cell Line	KB	Homo sapiens	ED50	=	0.4	ug ml-1	PMID[494609]
NPT168	Cell Line	P388	Mus musculus	ED50	=	0.2	ug ml-1	PMID[494609]
NPT140	Organism	Artemia	Artemia	LC50	=	21.3	ppm	PMID[494608]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	2.1	ug ml-1	PMID[494608]
NPT141	Organism	Agrobacterium tumefaciens	Agrobacterium tumefaciens	Inhibition	=	51.0	%	PMID[494608]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	0.3	ug ml-1	PMID[494609]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	0.4	ug ml-1	PMID[494609]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	0.7	ug ml-1	PMID[494609]

☑ 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 NPC475960 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	205
0.1-0.2	1121
0.2-0.3	4303
0.3-0.4	8093
0.4-0.5	13844
0.5-0.6	8461
0.6-0.7	5377
0.7-0.8	1257
0.8-0.85	32
0.85-0.9	0
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9697	High Similarity	NPC474917
0.9118	High Similarity	NPC305157
0.9118	High Similarity	NPC307846
0.8468	Intermediate Similarity	NPC277583
0.8416	Intermediate Similarity	NPC475927
0.8416	Intermediate Similarity	NPC475832
0.8396	Intermediate Similarity	NPC203659
0.8317	Intermediate Similarity	NPC179746
0.8317	Intermediate Similarity	NPC81419
0.8302	Intermediate Similarity	NPC475871
0.8302	Intermediate Similarity	NPC475945
0.8302	Intermediate Similarity	NPC110989
0.8269	Intermediate Similarity	NPC187268
0.8241	Intermediate Similarity	NPC474285
0.8241	Intermediate Similarity	NPC254538
0.8224	Intermediate Similarity	NPC100487
0.8218	Intermediate Similarity	NPC300312
0.8218	Intermediate Similarity	NPC12172
0.8218	Intermediate Similarity	NPC208886
0.8218	Intermediate Similarity	NPC261607
0.8218	Intermediate Similarity	NPC111114
0.8208	Intermediate Similarity	NPC225353
0.8208	Intermediate Similarity	NPC474747
0.8208	Intermediate Similarity	NPC86077
0.819	Intermediate Similarity	NPC288876
0.8173	Intermediate Similarity	NPC40812
0.8155	Intermediate Similarity	NPC304886
0.8148	Intermediate Similarity	NPC469401
0.8137	Intermediate Similarity	NPC475912
0.8113	Intermediate Similarity	NPC474742
0.8108	Intermediate Similarity	NPC474750
0.8103	Intermediate Similarity	NPC470829
0.8103	Intermediate Similarity	NPC473228
0.8095	Intermediate Similarity	NPC187761
0.8095	Intermediate Similarity	NPC255592
0.8095	Intermediate Similarity	NPC473326
0.8095	Intermediate Similarity	NPC308567
0.8095	Intermediate Similarity	NPC261377
0.8095	Intermediate Similarity	NPC83895
0.8095	Intermediate Similarity	NPC279561
0.8077	Intermediate Similarity	NPC473859
0.8077	Intermediate Similarity	NPC306041
0.8058	Intermediate Similarity	NPC71589
0.8058	Intermediate Similarity	NPC474338
0.8056	Intermediate Similarity	NPC474741
0.8039	Intermediate Similarity	NPC30515
0.8039	Intermediate Similarity	NPC470379
0.8039	Intermediate Similarity	NPC184463
0.8039	Intermediate Similarity	NPC470373
0.8037	Intermediate Similarity	NPC149371
0.8037	Intermediate Similarity	NPC13171
0.8037	Intermediate Similarity	NPC195510
0.8019	Intermediate Similarity	NPC469402
0.8018	Intermediate Similarity	NPC235014
0.8	Intermediate Similarity	NPC475309
0.8	Intermediate Similarity	NPC10150
0.8	Intermediate Similarity	NPC13710
0.8	Intermediate Similarity	NPC471462
0.8	Intermediate Similarity	NPC266842
0.7982	Intermediate Similarity	NPC243998
0.7981	Intermediate Similarity	NPC475659
0.7981	Intermediate Similarity	NPC193645
0.7981	Intermediate Similarity	NPC471142
0.7981	Intermediate Similarity	NPC48803
0.7981	Intermediate Similarity	NPC275960
0.7981	Intermediate Similarity	NPC90121
0.7981	Intermediate Similarity	NPC14961
0.7981	Intermediate Similarity	NPC36954
0.7981	Intermediate Similarity	NPC270013
0.7963	Intermediate Similarity	NPC472747
0.7963	Intermediate Similarity	NPC472750
0.7961	Intermediate Similarity	NPC212486
0.7961	Intermediate Similarity	NPC476300
0.7961	Intermediate Similarity	NPC135776
0.7944	Intermediate Similarity	NPC185141
0.7944	Intermediate Similarity	NPC110443
0.7944	Intermediate Similarity	NPC473332
0.7944	Intermediate Similarity	NPC133907
0.7944	Intermediate Similarity	NPC47880
0.7944	Intermediate Similarity	NPC46998
0.7944	Intermediate Similarity	NPC128733
0.7941	Intermediate Similarity	NPC71533
0.7941	Intermediate Similarity	NPC51004
0.7941	Intermediate Similarity	NPC106510
0.7928	Intermediate Similarity	NPC187876
0.7925	Intermediate Similarity	NPC208233
0.7925	Intermediate Similarity	NPC141191
0.7925	Intermediate Similarity	NPC472015
0.7925	Intermediate Similarity	NPC471144
0.7921	Intermediate Similarity	NPC202672
0.7905	Intermediate Similarity	NPC476315
0.7905	Intermediate Similarity	NPC54731
0.789	Intermediate Similarity	NPC472748
0.7885	Intermediate Similarity	NPC474035
0.7885	Intermediate Similarity	NPC477131
0.7885	Intermediate Similarity	NPC81386
0.7885	Intermediate Similarity	NPC303942
0.7885	Intermediate Similarity	NPC57405
0.787	Intermediate Similarity	NPC261117
0.787	Intermediate Similarity	NPC80144
0.787	Intermediate Similarity	NPC310804
0.7864	Intermediate Similarity	NPC131209
0.7843	Intermediate Similarity	NPC307411
0.7843	Intermediate Similarity	NPC295312
0.7843	Intermediate Similarity	NPC205548
0.7843	Intermediate Similarity	NPC473564
0.783	Intermediate Similarity	NPC476613
0.783	Intermediate Similarity	NPC169205
0.783	Intermediate Similarity	NPC472290
0.783	Intermediate Similarity	NPC476612
0.7822	Intermediate Similarity	NPC186148
0.7818	Intermediate Similarity	NPC472751
0.7818	Intermediate Similarity	NPC314244
0.7818	Intermediate Similarity	NPC472749
0.7818	Intermediate Similarity	NPC223450
0.781	Intermediate Similarity	NPC477922
0.7798	Intermediate Similarity	NPC475873
0.7778	Intermediate Similarity	NPC201718
0.7778	Intermediate Similarity	NPC472753
0.7778	Intermediate Similarity	NPC67296
0.7769	Intermediate Similarity	NPC298841
0.7768	Intermediate Similarity	NPC38154
0.7768	Intermediate Similarity	NPC315836
0.7768	Intermediate Similarity	NPC313668
0.7767	Intermediate Similarity	NPC206614
0.7767	Intermediate Similarity	NPC473619
0.7767	Intermediate Similarity	NPC475855
0.7767	Intermediate Similarity	NPC474761
0.7767	Intermediate Similarity	NPC80875
0.7767	Intermediate Similarity	NPC476004
0.7767	Intermediate Similarity	NPC474323
0.7759	Intermediate Similarity	NPC471145
0.7759	Intermediate Similarity	NPC471146
0.7759	Intermediate Similarity	NPC23046
0.7759	Intermediate Similarity	NPC475323
0.7757	Intermediate Similarity	NPC49833
0.7757	Intermediate Similarity	NPC249171
0.7757	Intermediate Similarity	NPC203627
0.7748	Intermediate Similarity	NPC477513
0.7748	Intermediate Similarity	NPC26617
0.7745	Intermediate Similarity	NPC58219
0.7745	Intermediate Similarity	NPC177629
0.7736	Intermediate Similarity	NPC230800
0.7736	Intermediate Similarity	NPC185553
0.7736	Intermediate Similarity	NPC279621
0.7736	Intermediate Similarity	NPC35498
0.7736	Intermediate Similarity	NPC477921
0.7731	Intermediate Similarity	NPC287236
0.7727	Intermediate Similarity	NPC469869
0.7727	Intermediate Similarity	NPC296950
0.7727	Intermediate Similarity	NPC86095
0.7714	Intermediate Similarity	NPC473316
0.7714	Intermediate Similarity	NPC470010
0.7714	Intermediate Similarity	NPC167219
0.7714	Intermediate Similarity	NPC262133
0.7714	Intermediate Similarity	NPC473330
0.7714	Intermediate Similarity	NPC470013
0.7714	Intermediate Similarity	NPC140543
0.7714	Intermediate Similarity	NPC323008
0.7714	Intermediate Similarity	NPC289004
0.7714	Intermediate Similarity	NPC476267
0.7712	Intermediate Similarity	NPC48692
0.7706	Intermediate Similarity	NPC472754
0.7706	Intermediate Similarity	NPC250545
0.7705	Intermediate Similarity	NPC473620
0.7699	Intermediate Similarity	NPC46407
0.7699	Intermediate Similarity	NPC5103
0.7692	Intermediate Similarity	NPC473321
0.7692	Intermediate Similarity	NPC9447
0.7692	Intermediate Similarity	NPC133698
0.7685	Intermediate Similarity	NPC475053
0.7685	Intermediate Similarity	NPC473146
0.7685	Intermediate Similarity	NPC70865
0.7679	Intermediate Similarity	NPC177524
0.7679	Intermediate Similarity	NPC392
0.7679	Intermediate Similarity	NPC219900
0.767	Intermediate Similarity	NPC32922
0.767	Intermediate Similarity	NPC92974
0.767	Intermediate Similarity	NPC474032
0.7667	Intermediate Similarity	NPC186339
0.7664	Intermediate Similarity	NPC304445
0.7664	Intermediate Similarity	NPC236580
0.7661	Intermediate Similarity	NPC475139
0.7661	Intermediate Similarity	NPC180902
0.7658	Intermediate Similarity	NPC239961
0.7658	Intermediate Similarity	NPC153095
0.7658	Intermediate Similarity	NPC476738
0.7658	Intermediate Similarity	NPC476740
0.7652	Intermediate Similarity	NPC264153
0.7647	Intermediate Similarity	NPC231889
0.7647	Intermediate Similarity	NPC160138
0.7647	Intermediate Similarity	NPC190753
0.7647	Intermediate Similarity	NPC469812
0.7647	Intermediate Similarity	NPC170880
0.7647	Intermediate Similarity	NPC183353
0.7642	Intermediate Similarity	NPC272050
0.7642	Intermediate Similarity	NPC52044
0.7642	Intermediate Similarity	NPC471141
0.7636	Intermediate Similarity	NPC309398
0.7636	Intermediate Similarity	NPC4620

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 NPC475960 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	173
0.1-0.2	1486
0.2-0.3	3743
0.3-0.4	2469
0.4-0.5	803
0.5-0.6	328
0.6-0.7	127
0.7-0.8	21
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
0.7981	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7748	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7679	Intermediate Similarity	NPD6686	Approved
0.7647	Intermediate Similarity	NPD8516	Approved
0.7647	Intermediate Similarity	NPD8517	Approved
0.7647	Intermediate Similarity	NPD8513	Phase 3
0.7647	Intermediate Similarity	NPD8515	Approved
0.7431	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD46	Approved
0.7429	Intermediate Similarity	NPD6698	Approved
0.7391	Intermediate Similarity	NPD6371	Approved
0.7383	Intermediate Similarity	NPD5282	Discontinued
0.7328	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7236	Intermediate Similarity	NPD7642	Approved
0.7222	Intermediate Similarity	NPD7319	Approved
0.7196	Intermediate Similarity	NPD7983	Approved
0.717	Intermediate Similarity	NPD1695	Approved
0.712	Intermediate Similarity	NPD7507	Approved
0.7097	Intermediate Similarity	NPD7829	Approved
0.7097	Intermediate Similarity	NPD7830	Approved
0.7063	Intermediate Similarity	NPD8074	Phase 3
0.7016	Intermediate Similarity	NPD6370	Approved
0.7008	Intermediate Similarity	NPD7736	Approved
0.6984	Remote Similarity	NPD8451	Approved
0.6972	Remote Similarity	NPD5778	Approved
0.6972	Remote Similarity	NPD5779	Approved
0.697	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD4225	Approved
0.6944	Remote Similarity	NPD7838	Discovery
0.6937	Remote Similarity	NPD7839	Suspended
0.6929	Remote Similarity	NPD8448	Approved
0.6929	Remote Similarity	NPD7078	Approved
0.6905	Remote Similarity	NPD7492	Approved
0.6855	Remote Similarity	NPD6054	Approved
0.685	Remote Similarity	NPD6616	Approved
0.6833	Remote Similarity	NPD6053	Discontinued
0.6829	Remote Similarity	NPD7641	Discontinued
0.68	Remote Similarity	NPD6016	Approved
0.68	Remote Similarity	NPD8444	Approved
0.68	Remote Similarity	NPD6015	Approved
0.6797	Remote Similarity	NPD8293	Discontinued
0.6789	Remote Similarity	NPD5785	Approved
0.6772	Remote Similarity	NPD8340	Approved
0.6772	Remote Similarity	NPD8299	Approved
0.6772	Remote Similarity	NPD8341	Approved
0.6772	Remote Similarity	NPD8342	Approved
0.6769	Remote Similarity	NPD8391	Approved
0.6769	Remote Similarity	NPD8390	Approved
0.6769	Remote Similarity	NPD8392	Approved
0.6746	Remote Similarity	NPD5988	Approved
0.6697	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD6101	Approved
0.6696	Remote Similarity	NPD5344	Discontinued
0.6695	Remote Similarity	NPD6412	Phase 2
0.6693	Remote Similarity	NPD8328	Phase 3
0.6636	Remote Similarity	NPD5363	Approved
0.6613	Remote Similarity	NPD7115	Discovery
0.6587	Remote Similarity	NPD6059	Approved
0.6577	Remote Similarity	NPD6411	Approved
0.6574	Remote Similarity	NPD4249	Approved
0.6574	Remote Similarity	NPD5786	Approved
0.656	Remote Similarity	NPD7328	Approved
0.656	Remote Similarity	NPD7327	Approved
0.6535	Remote Similarity	NPD7503	Approved
0.6535	Remote Similarity	NPD8269	Approved
0.6535	Remote Similarity	NPD8268	Approved
0.6535	Remote Similarity	NPD8033	Approved
0.6535	Remote Similarity	NPD8266	Approved
0.6535	Remote Similarity	NPD8267	Approved
0.6514	Remote Similarity	NPD4251	Approved
0.6514	Remote Similarity	NPD4250	Approved
0.6508	Remote Similarity	NPD7516	Approved
0.65	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD8080	Discontinued
0.6481	Remote Similarity	NPD1694	Approved
0.648	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.648	Remote Similarity	NPD6009	Approved
0.648	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6466	Remote Similarity	NPD6648	Approved
0.6457	Remote Similarity	NPD8377	Approved
0.6457	Remote Similarity	NPD8294	Approved
0.6457	Remote Similarity	NPD6319	Approved
0.6449	Remote Similarity	NPD5362	Discontinued
0.6449	Remote Similarity	NPD7154	Phase 3
0.6415	Remote Similarity	NPD5369	Approved
0.6406	Remote Similarity	NPD8378	Approved
0.6406	Remote Similarity	NPD8296	Approved
0.6406	Remote Similarity	NPD8380	Approved
0.6406	Remote Similarity	NPD8335	Approved
0.6406	Remote Similarity	NPD8379	Approved
0.6371	Remote Similarity	NPD8133	Approved
0.6355	Remote Similarity	NPD6435	Approved
0.6355	Remote Similarity	NPD4269	Approved
0.6355	Remote Similarity	NPD4270	Approved
0.6311	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.629	Remote Similarity	NPD6882	Approved
0.6279	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.626	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.625	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.625	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.6241	Remote Similarity	NPD8337	Approved
0.6241	Remote Similarity	NPD8336	Approved
0.624	Remote Similarity	NPD4632	Approved
0.6239	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD7638	Approved
0.6222	Remote Similarity	NPD7260	Phase 2
0.6204	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6204	Remote Similarity	NPD5209	Approved
0.6198	Remote Similarity	NPD6008	Approved
0.6186	Remote Similarity	NPD7639	Approved
0.6186	Remote Similarity	NPD7640	Approved
0.6182	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6179	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD8338	Approved
0.6168	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6168	Remote Similarity	NPD5368	Approved
0.6168	Remote Similarity	NPD4821	Approved
0.6168	Remote Similarity	NPD4822	Approved
0.6168	Remote Similarity	NPD4820	Approved
0.6168	Remote Similarity	NPD4819	Approved
0.6168	Remote Similarity	NPD4252	Approved
0.616	Remote Similarity	NPD8297	Approved
0.6148	Remote Similarity	NPD5697	Approved
0.6148	Remote Similarity	NPD5956	Approved
0.614	Remote Similarity	NPD7637	Suspended
0.6119	Remote Similarity	NPD6033	Approved
0.6098	Remote Similarity	NPD6881	Approved
0.6098	Remote Similarity	NPD6899	Approved
0.6094	Remote Similarity	NPD7500	Approved
0.609	Remote Similarity	NPD8273	Phase 1
0.608	Remote Similarity	NPD6650	Approved
0.608	Remote Similarity	NPD6649	Approved
0.6058	Remote Similarity	NPD6845	Suspended
0.6048	Remote Similarity	NPD6014	Approved
0.6048	Remote Similarity	NPD6013	Approved
0.6048	Remote Similarity	NPD6012	Approved
0.6031	Remote Similarity	NPD5983	Phase 2
0.6016	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6	Remote Similarity	NPD4634	Approved
0.6	Remote Similarity	NPD7102	Approved
0.6	Remote Similarity	NPD7290	Approved
0.6	Remote Similarity	NPD6883	Approved
0.5981	Remote Similarity	NPD4271	Approved
0.5981	Remote Similarity	NPD4268	Approved
0.5968	Remote Similarity	NPD7320	Approved
0.5968	Remote Similarity	NPD6011	Approved
0.5963	Remote Similarity	NPD4790	Discontinued
0.5952	Remote Similarity	NPD6847	Approved
0.5952	Remote Similarity	NPD8130	Phase 1
0.5952	Remote Similarity	NPD6869	Approved
0.5952	Remote Similarity	NPD2204	Approved
0.5952	Remote Similarity	NPD6617	Approved
0.594	Remote Similarity	NPD7604	Phase 2
0.594	Remote Similarity	NPD6067	Discontinued
0.5935	Remote Similarity	NPD5739	Approved
0.5935	Remote Similarity	NPD6675	Approved
0.5935	Remote Similarity	NPD7128	Approved
0.5935	Remote Similarity	NPD6402	Approved
0.592	Remote Similarity	NPD6373	Approved
0.592	Remote Similarity	NPD6372	Approved
0.5909	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD6921	Approved
0.5906	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.5887	Remote Similarity	NPD5701	Approved
0.5857	Remote Similarity	NPD8415	Approved
0.5856	Remote Similarity	NPD6110	Phase 1
0.5856	Remote Similarity	NPD5332	Approved
0.5856	Remote Similarity	NPD5331	Approved
0.5852	Remote Similarity	NPD6336	Discontinued
0.5833	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5821	Remote Similarity	NPD7122	Discontinued
0.582	Remote Similarity	NPD5211	Phase 2
0.582	Remote Similarity	NPD8083	Approved
0.582	Remote Similarity	NPD8082	Approved
0.582	Remote Similarity	NPD8086	Approved
0.582	Remote Similarity	NPD8084	Approved
0.582	Remote Similarity	NPD8139	Approved
0.582	Remote Similarity	NPD8085	Approved
0.582	Remote Similarity	NPD8138	Approved
0.5816	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.5812	Remote Similarity	NPD6399	Phase 3
0.5802	Remote Similarity	NPD7799	Discontinued
0.5797	Remote Similarity	NPD6914	Discontinued
0.5789	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.5785	Remote Similarity	NPD5285	Approved
0.5785	Remote Similarity	NPD5286	Approved
0.5785	Remote Similarity	NPD4696	Approved
0.5772	Remote Similarity	NPD8276	Approved
0.5772	Remote Similarity	NPD8275	Approved
0.575	Remote Similarity	NPD6083	Phase 2
0.575	Remote Similarity	NPD6084	Phase 2
0.5738	Remote Similarity	NPD1700	Approved
0.5726	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.5726	Remote Similarity	NPD8081	Approved
0.5726	Remote Similarity	NPD5141	Approved
0.5714	Remote Similarity	NPD5695	Phase 3
0.5703	Remote Similarity	NPD1719	Phase 1
0.5703	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.5702	Remote Similarity	NPD5696	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