NPASS Compound

Structure

NPC474951 OpenBabel07101718312D 29 31 0 0 1 0 0 0 0 0999 V2000 -0.8655 1.0366 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3625 3.1348 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7787 -2.3081 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7914 -0.7547 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0793 1.4950 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7081 0.4100 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9668 -1.4787 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4471 -0.7238 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3910 -1.5219 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8783 -0.1418 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5962 0.2651 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7778 1.0443 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6917 0.4732 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0678 2.1792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3153 0.8333 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4669 -1.1900 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4606 -0.8876 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2019 1.0011 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5844 -0.2388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8534 -1.3109 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.7922 -0.7129 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7018 0.7124 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7480 1.4462 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1471 -1.9230 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6288 -0.5336 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0475 -1.7448 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9071 1.9567 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 -2.0742 -0.7667 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 2 0 0 0 0 2 14 1 0 0 0 0 6 10 1 0 0 0 0 7 9 1 0 0 0 0 7 16 1 0 0 0 0 8 11 1 0 0 0 0 8 17 1 0 0 0 0 9 20 1 0 0 0 0 10 21 1 0 0 0 0 11 22 1 0 0 0 0 12 15 1 0 0 0 0 12 18 1 0 0 0 0 13 15 1 0 0 0 0 13 19 1 0 0 0 0 14 23 2 0 0 0 0 14 27 1 0 0 0 0 15 6 1 6 0 0 0 16 21 1 0 0 0 0 16 24 2 0 0 0 0 17 20 1 6 0 0 0 17 28 1 0 0 0 0 18 22 1 6 0 0 0 18 27 1 0 0 0 0 19 25 2 0 0 0 0 19 29 1 0 0 0 0 20 3 1 1 0 0 0 20 26 1 0 0 0 0 21 4 1 6 0 0 0 21 29 1 0 0 0 0 22 5 1 1 0 0 0 22 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	408.21
Volume:	414.385
LogP:	2.01
LogD:	1.436
LogS:	-3.987
# Rotatable Bonds:	2
TPSA:	99.13
# H-Bond Aceptor:	7
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.526
Synthetic Accessibility Score:	6.267
Fsp3:	0.773
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.754
MDCK Permeability:	2.6463018002687022e-05
Pgp-inhibitor:	0.992
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.927
30% Bioavailability (F30%):	0.843

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.493
Plasma Protein Binding (PPB):	76.41992950439453%
Volume Distribution (VD):	0.997
Pgp-substrate:	24.34449005126953%

ADMET: Metabolism

CYP1A2-inhibitor:	0.01
CYP1A2-substrate:	0.129
CYP2C19-inhibitor:	0.026
CYP2C19-substrate:	0.584
CYP2C9-inhibitor:	0.071
CYP2C9-substrate:	0.078
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.208
CYP3A4-inhibitor:	0.344
CYP3A4-substrate:	0.255

ADMET: Excretion

Clearance (CL):	4.305
Half-life (T1/2):	0.814

ADMET: Toxicity

hERG Blockers:	0.026
Human Hepatotoxicity (H-HT):	0.616
Drug-inuced Liver Injury (DILI):	0.796
AMES Toxicity:	0.195
Rat Oral Acute Toxicity:	0.057
Maximum Recommended Daily Dose:	0.621
Skin Sensitization:	0.817
Carcinogencity:	0.412
Eye Corrosion:	0.042
Eye Irritation:	0.156
Respiratory Toxicity:	0.326

Download Data

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

Natural Product: NPC474951

Natural Product ID:	NPC474951
*Common Name:**	ADEVBUKPYQGFGW-ZVNQDOHQSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	ADEVBUKPYQGFGW-ZVNQDOHQSA-N
Standard InCHI:	InChI=1S/C22H32O7/c1-13-15-6-10-21(4,29-19(13)25)16(24)7-9-20(3,26)17-8-11-22(5,28-17)18(12-15)27-14(2)23/h15,17-18,26H,1,6-12H2,2-5H3/t15-,17+,18+,20-,21-,22-/m1/s1
SMILES:	CC(=O)OC1CC2CCC(C(=O)CCC(C3CCC1(O3)C)(C)O)(OC(=O)C2=C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL490019
PubChem CID:	23246247
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000147] Macrolides and analogues

*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
NPO9060	Sinularia granosa	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18831569]
NPO7475	Sinularia querciformis	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18831569]
NPO9060	Sinularia granosa	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[22672798]
NPO9060	Sinularia granosa	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7475	Sinularia querciformis	Species	Alcyoniidae	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	4
IC50	3
Others	2

Activity Type	# Activity
Cell Line	7
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell Line	HeLa	Homo sapiens	IC50	>	20.0	ug.mL-1	PMID[525561]
NPT1171	Cell Line	HEp-2	Homo sapiens	IC50	>	20.0	ug.mL-1	PMID[525561]
NPT165	Cell Line	HeLa	Homo sapiens	ED50	<	20.0	ug ml-1	PMID[525561]
NPT1171	Cell Line	HEp-2	Homo sapiens	ED50	<	20.0	ug ml-1	PMID[525561]
NPT83	Cell Line	MCF7	Homo sapiens	ED50	<	20.0	ug ml-1	PMID[525561]
NPT113	Cell Line	RAW264.7	Mus musculus	Activity	=	20.3	%	PMID[525561]
NPT113	Cell Line	RAW264.7	Mus musculus	Activity	=	14.0	%	PMID[525561]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	20.0	ug.mL-1	PMID[525561]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	<	20.0	ug ml-1	PMID[525561]

☑ 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 NPC474951 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	237
0.1-0.2	1844
0.2-0.3	6419
0.3-0.4	13898
0.4-0.5	10514
0.5-0.6	6731
0.6-0.7	2453
0.7-0.8	520
0.8-0.85	64
0.85-0.9	8
0.9-0.95	7
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9762	High Similarity	NPC173926
0.931	High Similarity	NPC329952
0.9286	High Similarity	NPC329749
0.9176	High Similarity	NPC475019
0.9176	High Similarity	NPC476015
0.9176	High Similarity	NPC474762
0.9176	High Similarity	NPC474949
0.9	High Similarity	NPC475900
0.8941	High Similarity	NPC474780
0.8916	High Similarity	NPC474981
0.8901	High Similarity	NPC31645
0.8889	High Similarity	NPC190294
0.8837	High Similarity	NPC304509
0.8837	High Similarity	NPC149725
0.8837	High Similarity	NPC47958
0.8804	High Similarity	NPC323421
0.8804	High Similarity	NPC328562
0.875	High Similarity	NPC177629
0.875	High Similarity	NPC58219
0.8696	High Similarity	NPC76862
0.8696	High Similarity	NPC470883
0.8696	High Similarity	NPC39859
0.8696	High Similarity	NPC476009
0.8696	High Similarity	NPC158416
0.8652	High Similarity	NPC92974
0.8652	High Similarity	NPC307411
0.8636	High Similarity	NPC186148
0.8636	High Similarity	NPC248602
0.8605	High Similarity	NPC474472
0.8605	High Similarity	NPC257358
0.8556	High Similarity	NPC51004
0.8526	High Similarity	NPC15993
0.8506	High Similarity	NPC475963
0.8506	High Similarity	NPC3464
0.8506	High Similarity	NPC151176
0.8462	Intermediate Similarity	NPC184463
0.8462	Intermediate Similarity	NPC30515
0.8438	Intermediate Similarity	NPC320019
0.8438	Intermediate Similarity	NPC324017
0.8427	Intermediate Similarity	NPC190753
0.837	Intermediate Similarity	NPC476300
0.8352	Intermediate Similarity	NPC474761
0.8352	Intermediate Similarity	NPC476004
0.8333	Intermediate Similarity	NPC474742
0.8333	Intermediate Similarity	NPC153805
0.8333	Intermediate Similarity	NPC476270
0.8333	Intermediate Similarity	NPC227379
0.8333	Intermediate Similarity	NPC281516
0.8333	Intermediate Similarity	NPC474471
0.8333	Intermediate Similarity	NPC202672
0.8261	Intermediate Similarity	NPC12172
0.8261	Intermediate Similarity	NPC208886
0.8247	Intermediate Similarity	NPC474747
0.8222	Intermediate Similarity	NPC118601
0.8191	Intermediate Similarity	NPC36954
0.8191	Intermediate Similarity	NPC163228
0.8182	Intermediate Similarity	NPC11620
0.8182	Intermediate Similarity	NPC128429
0.8172	Intermediate Similarity	NPC475912
0.8172	Intermediate Similarity	NPC179746
0.8172	Intermediate Similarity	NPC81419
0.8172	Intermediate Similarity	NPC212486
0.8163	Intermediate Similarity	NPC475945
0.8163	Intermediate Similarity	NPC475871
0.8163	Intermediate Similarity	NPC475873
0.8152	Intermediate Similarity	NPC65359
0.8144	Intermediate Similarity	NPC47880
0.8144	Intermediate Similarity	NPC201718
0.8132	Intermediate Similarity	NPC178875
0.8111	Intermediate Similarity	NPC470242
0.8085	Intermediate Similarity	NPC81386
0.8085	Intermediate Similarity	NPC474035
0.8081	Intermediate Similarity	NPC474741
0.8065	Intermediate Similarity	NPC70251
0.8065	Intermediate Similarity	NPC475881
0.8065	Intermediate Similarity	NPC469627
0.8061	Intermediate Similarity	NPC149371
0.8022	Intermediate Similarity	NPC5130
0.8022	Intermediate Similarity	NPC179659
0.8021	Intermediate Similarity	NPC474313
0.8021	Intermediate Similarity	NPC471150
0.8	Intermediate Similarity	NPC14961
0.8	Intermediate Similarity	NPC137033
0.8	Intermediate Similarity	NPC270013
0.798	Intermediate Similarity	NPC472755
0.7959	Intermediate Similarity	NPC472753
0.7959	Intermediate Similarity	NPC474339
0.7959	Intermediate Similarity	NPC164598
0.7957	Intermediate Similarity	NPC469718
0.7957	Intermediate Similarity	NPC474323
0.7957	Intermediate Similarity	NPC206614
0.7957	Intermediate Similarity	NPC329857
0.7917	Intermediate Similarity	NPC476315
0.7889	Intermediate Similarity	NPC9868
0.7879	Intermediate Similarity	NPC472754
0.7872	Intermediate Similarity	NPC20713
0.7857	Intermediate Similarity	NPC186861
0.7849	Intermediate Similarity	NPC474032
0.7826	Intermediate Similarity	NPC231889
0.7812	Intermediate Similarity	NPC474947
0.7802	Intermediate Similarity	NPC21469
0.78	Intermediate Similarity	NPC472750
0.78	Intermediate Similarity	NPC472747
0.7789	Intermediate Similarity	NPC473273
0.7789	Intermediate Similarity	NPC473263
0.7789	Intermediate Similarity	NPC135776
0.7789	Intermediate Similarity	NPC153590
0.7789	Intermediate Similarity	NPC473234
0.7789	Intermediate Similarity	NPC308656
0.7789	Intermediate Similarity	NPC60386
0.7778	Intermediate Similarity	NPC185141
0.7778	Intermediate Similarity	NPC133907
0.7778	Intermediate Similarity	NPC110443
0.7778	Intermediate Similarity	NPC46998
0.7778	Intermediate Similarity	NPC128733
0.7767	Intermediate Similarity	NPC38154
0.7766	Intermediate Similarity	NPC475748
0.7755	Intermediate Similarity	NPC474213
0.7755	Intermediate Similarity	NPC471144
0.7745	Intermediate Similarity	NPC477513
0.7742	Intermediate Similarity	NPC53158
0.7723	Intermediate Similarity	NPC100487
0.7723	Intermediate Similarity	NPC472756
0.7723	Intermediate Similarity	NPC472748
0.7717	Intermediate Similarity	NPC164393
0.7717	Intermediate Similarity	NPC469626
0.7717	Intermediate Similarity	NPC162071
0.7717	Intermediate Similarity	NPC475491
0.7708	Intermediate Similarity	NPC121825
0.7708	Intermediate Similarity	NPC473331
0.77	Intermediate Similarity	NPC471148
0.77	Intermediate Similarity	NPC225353
0.7692	Intermediate Similarity	NPC72464
0.7677	Intermediate Similarity	NPC475949
0.7677	Intermediate Similarity	NPC471381
0.767	Intermediate Similarity	NPC255082
0.766	Intermediate Similarity	NPC295312
0.766	Intermediate Similarity	NPC151770
0.7647	Intermediate Similarity	NPC44004
0.7647	Intermediate Similarity	NPC472749
0.7647	Intermediate Similarity	NPC472751
0.764	Intermediate Similarity	NPC233377
0.7629	Intermediate Similarity	NPC322188
0.7629	Intermediate Similarity	NPC472873
0.7629	Intermediate Similarity	NPC476053
0.7629	Intermediate Similarity	NPC475659
0.7624	Intermediate Similarity	NPC110989
0.7624	Intermediate Similarity	NPC473148
0.7609	Intermediate Similarity	NPC300082
0.7609	Intermediate Similarity	NPC99395
0.7609	Intermediate Similarity	NPC284534
0.7609	Intermediate Similarity	NPC197903
0.7609	Intermediate Similarity	NPC204105
0.7604	Intermediate Similarity	NPC475788
0.7604	Intermediate Similarity	NPC295204
0.7604	Intermediate Similarity	NPC469692
0.7604	Intermediate Similarity	NPC469645
0.7604	Intermediate Similarity	NPC273579
0.7604	Intermediate Similarity	NPC200237
0.7604	Intermediate Similarity	NPC288240
0.7604	Intermediate Similarity	NPC162205
0.7593	Intermediate Similarity	NPC471146
0.7593	Intermediate Similarity	NPC471145
0.7582	Intermediate Similarity	NPC250315
0.7582	Intermediate Similarity	NPC272814
0.7579	Intermediate Similarity	NPC473619
0.7576	Intermediate Similarity	NPC473326
0.7573	Intermediate Similarity	NPC26617
0.7556	Intermediate Similarity	NPC47635
0.7553	Intermediate Similarity	NPC217983
0.7553	Intermediate Similarity	NPC207114
0.7553	Intermediate Similarity	NPC79549
0.7551	Intermediate Similarity	NPC473859
0.7551	Intermediate Similarity	NPC476275
0.7551	Intermediate Similarity	NPC91771
0.7551	Intermediate Similarity	NPC142529
0.7549	Intermediate Similarity	NPC203659
0.7528	Intermediate Similarity	NPC19841
0.7527	Intermediate Similarity	NPC67493
0.7527	Intermediate Similarity	NPC309757
0.7527	Intermediate Similarity	NPC236692
0.7527	Intermediate Similarity	NPC477010
0.7527	Intermediate Similarity	NPC284902
0.7526	Intermediate Similarity	NPC71589
0.7526	Intermediate Similarity	NPC476722
0.7526	Intermediate Similarity	NPC303942
0.7526	Intermediate Similarity	NPC57405
0.7526	Intermediate Similarity	NPC469632
0.75	Intermediate Similarity	NPC138647
0.75	Intermediate Similarity	NPC70424
0.75	Intermediate Similarity	NPC288876
0.75	Intermediate Similarity	NPC184063
0.75	Intermediate Similarity	NPC473321
0.75	Intermediate Similarity	NPC472958
0.75	Intermediate Similarity	NPC470379
0.75	Intermediate Similarity	NPC470238
0.75	Intermediate Similarity	NPC133698
0.75	Intermediate Similarity	NPC470373
0.75	Intermediate Similarity	NPC243618
0.75	Intermediate Similarity	NPC472957

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 NPC474951 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	278
0.1-0.2	2640
0.2-0.3	3737
0.3-0.4	1660
0.4-0.5	526
0.5-0.6	276
0.6-0.7	28
0.7-0.8	5
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
0.7573	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD46	Approved
0.7041	Intermediate Similarity	NPD6698	Approved
0.7037	Intermediate Similarity	NPD6371	Approved
0.6931	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.68	Remote Similarity	NPD7983	Approved
0.6768	Remote Similarity	NPD1695	Approved
0.67	Remote Similarity	NPD7838	Discovery
0.6545	Remote Similarity	NPD6686	Approved
0.6505	Remote Similarity	NPD5282	Discontinued
0.6495	Remote Similarity	NPD6110	Phase 1
0.646	Remote Similarity	NPD6053	Discontinued
0.6415	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD4632	Approved
0.6392	Remote Similarity	NPD6435	Approved
0.6392	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD5785	Approved
0.6356	Remote Similarity	NPD6319	Approved
0.6316	Remote Similarity	NPD8297	Approved
0.63	Remote Similarity	NPD5786	Approved
0.6289	Remote Similarity	NPD5369	Approved
0.6281	Remote Similarity	NPD7492	Approved
0.6262	Remote Similarity	NPD4225	Approved
0.625	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6881	Approved
0.625	Remote Similarity	NPD5779	Approved
0.625	Remote Similarity	NPD6899	Approved
0.625	Remote Similarity	NPD5778	Approved
0.6239	Remote Similarity	NPD6009	Approved
0.623	Remote Similarity	NPD6616	Approved
0.6228	Remote Similarity	NPD6650	Approved
0.6228	Remote Similarity	NPD6649	Approved
0.6218	Remote Similarity	NPD6054	Approved
0.6216	Remote Similarity	NPD6675	Approved
0.6216	Remote Similarity	NPD7128	Approved
0.6216	Remote Similarity	NPD6402	Approved
0.6216	Remote Similarity	NPD5739	Approved
0.62	Remote Similarity	NPD5363	Approved
0.62	Remote Similarity	NPD1694	Approved
0.6198	Remote Similarity	NPD7604	Phase 2
0.6195	Remote Similarity	NPD6372	Approved
0.6195	Remote Similarity	NPD6373	Approved
0.6186	Remote Similarity	NPD5368	Approved
0.6179	Remote Similarity	NPD7078	Approved
0.6168	Remote Similarity	NPD6084	Phase 2
0.6168	Remote Similarity	NPD6083	Phase 2
0.6167	Remote Similarity	NPD8266	Approved
0.6167	Remote Similarity	NPD8513	Phase 3
0.6167	Remote Similarity	NPD8267	Approved
0.6167	Remote Similarity	NPD8516	Approved
0.6167	Remote Similarity	NPD8268	Approved
0.6167	Remote Similarity	NPD8515	Approved
0.6167	Remote Similarity	NPD6921	Approved
0.6167	Remote Similarity	NPD5983	Phase 2
0.6167	Remote Similarity	NPD8269	Approved
0.6167	Remote Similarity	NPD8517	Approved
0.6162	Remote Similarity	NPD7154	Phase 3
0.6161	Remote Similarity	NPD5697	Approved
0.6147	Remote Similarity	NPD5344	Discontinued
0.614	Remote Similarity	NPD6883	Approved
0.614	Remote Similarity	NPD7290	Approved
0.614	Remote Similarity	NPD7102	Approved
0.6136	Remote Similarity	NPD7909	Approved
0.6132	Remote Similarity	NPD5695	Phase 3
0.6129	Remote Similarity	NPD7736	Approved
0.6121	Remote Similarity	NPD8133	Approved
0.6116	Remote Similarity	NPD6370	Approved
0.6111	Remote Similarity	NPD5696	Approved
0.6111	Remote Similarity	NPD7260	Phase 2
0.6111	Remote Similarity	NPD7638	Approved
0.6106	Remote Similarity	NPD6011	Approved
0.6106	Remote Similarity	NPD7320	Approved
0.6102	Remote Similarity	NPD7115	Discovery
0.6098	Remote Similarity	NPD6336	Discontinued
0.6087	Remote Similarity	NPD6617	Approved
0.6087	Remote Similarity	NPD6847	Approved
0.6087	Remote Similarity	NPD6869	Approved
0.6087	Remote Similarity	NPD8130	Phase 1
0.6083	Remote Similarity	NPD6059	Approved
0.6067	Remote Similarity	NPD7341	Phase 2
0.6066	Remote Similarity	NPD8328	Phase 3
0.6063	Remote Similarity	NPD6845	Suspended
0.6061	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD4270	Approved
0.6061	Remote Similarity	NPD4269	Approved
0.6055	Remote Similarity	NPD7640	Approved
0.6055	Remote Similarity	NPD7639	Approved
0.6053	Remote Similarity	NPD6013	Approved
0.6053	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6053	Remote Similarity	NPD6014	Approved
0.6053	Remote Similarity	NPD6012	Approved
0.6048	Remote Similarity	NPD8293	Discontinued
0.604	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6034	Remote Similarity	NPD6882	Approved
0.6033	Remote Similarity	NPD6016	Approved
0.6033	Remote Similarity	NPD6015	Approved
0.6019	Remote Similarity	NPD5737	Approved
0.6019	Remote Similarity	NPD6672	Approved
0.6018	Remote Similarity	NPD5701	Approved
0.6	Remote Similarity	NPD5362	Discontinued
0.6	Remote Similarity	NPD7331	Phase 2
0.6	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5693	Phase 1
0.5984	Remote Similarity	NPD5988	Approved
0.5984	Remote Similarity	NPD8080	Discontinued
0.5979	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5968	Remote Similarity	NPD7507	Approved
0.5962	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5962	Remote Similarity	NPD6101	Approved
0.5955	Remote Similarity	NPD3197	Phase 1
0.5948	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5943	Remote Similarity	NPD6399	Phase 3
0.5935	Remote Similarity	NPD7642	Approved
0.5929	Remote Similarity	NPD6008	Approved
0.5926	Remote Similarity	NPD7839	Suspended
0.5922	Remote Similarity	NPD4250	Approved
0.5922	Remote Similarity	NPD4251	Approved
0.592	Remote Similarity	NPD8074	Phase 3
0.5917	Remote Similarity	NPD7641	Discontinued
0.5909	Remote Similarity	NPD6648	Approved
0.5902	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.5877	Remote Similarity	NPD6412	Phase 2
0.5876	Remote Similarity	NPD4756	Discovery
0.5859	Remote Similarity	NPD4252	Approved
0.5849	Remote Similarity	NPD8034	Phase 2
0.5849	Remote Similarity	NPD6411	Approved
0.5849	Remote Similarity	NPD8035	Phase 2
0.5841	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.5841	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.5827	Remote Similarity	NPD7319	Approved
0.5825	Remote Similarity	NPD4249	Approved
0.5816	Remote Similarity	NPD4802	Phase 2
0.5816	Remote Similarity	NPD4238	Approved
0.581	Remote Similarity	NPD6673	Approved
0.581	Remote Similarity	NPD6080	Approved
0.581	Remote Similarity	NPD6904	Approved
0.5785	Remote Similarity	NPD6335	Approved
0.575	Remote Similarity	NPD6868	Approved
0.575	Remote Similarity	NPD6274	Approved
0.5748	Remote Similarity	NPD6033	Approved
0.5743	Remote Similarity	NPD5209	Approved
0.5741	Remote Similarity	NPD7748	Approved
0.5739	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5738	Remote Similarity	NPD7100	Approved
0.5738	Remote Similarity	NPD7101	Approved
0.5727	Remote Similarity	NPD7902	Approved
0.5726	Remote Similarity	NPD4634	Approved
0.5714	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD1700	Approved
0.5714	Remote Similarity	NPD8451	Approved
0.5702	Remote Similarity	NPD6317	Approved
0.5701	Remote Similarity	NPD6050	Approved
0.57	Remote Similarity	NPD4820	Approved
0.57	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.57	Remote Similarity	NPD4819	Approved
0.57	Remote Similarity	NPD4821	Approved
0.57	Remote Similarity	NPD4822	Approved
0.5686	Remote Similarity	NPD4788	Approved
0.5682	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.568	Remote Similarity	NPD7830	Approved
0.568	Remote Similarity	NPD7829	Approved
0.5678	Remote Similarity	NPD2204	Approved
0.5673	Remote Similarity	NPD7146	Approved
0.5673	Remote Similarity	NPD6422	Discontinued
0.5673	Remote Similarity	NPD7521	Approved
0.5673	Remote Similarity	NPD6684	Approved
0.5673	Remote Similarity	NPD7334	Approved
0.5673	Remote Similarity	NPD6098	Approved
0.5673	Remote Similarity	NPD6409	Approved
0.5673	Remote Similarity	NPD5330	Approved
0.567	Remote Similarity	NPD8039	Approved
0.5669	Remote Similarity	NPD8448	Approved
0.5664	Remote Similarity	NPD5211	Phase 2
0.5664	Remote Similarity	NPD7632	Discontinued
0.5656	Remote Similarity	NPD6314	Approved
0.5656	Remote Similarity	NPD6313	Approved
0.5647	Remote Similarity	NPD3730	Approved
0.5647	Remote Similarity	NPD3728	Approved
0.5645	Remote Similarity	NPD8444	Approved
0.5645	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.5641	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.5636	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5636	Remote Similarity	NPD5221	Approved
0.5636	Remote Similarity	NPD5222	Approved
0.5636	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5636	Remote Similarity	NPD4697	Phase 3
0.5625	Remote Similarity	NPD5285	Approved
0.5625	Remote Similarity	NPD4696	Approved
0.5625	Remote Similarity	NPD5286	Approved
0.5607	Remote Similarity	NPD5692	Phase 3
0.5606	Remote Similarity	NPD8415	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