NPASS Compound

Structure

NPC474765 OpenBabel07101719132D 30 31 0 0 1 0 0 0 0 0999 V2000 -3.8756 1.4866 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3149 -2.6942 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7076 -5.1447 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7824 -4.9816 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3603 -2.2672 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8258 0.8135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3425 1.3524 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7125 -2.4117 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8298 -2.7330 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4174 1.1893 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3425 -1.3524 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4174 -1.1893 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6411 -0.8440 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1560 0.8827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1976 -2.3729 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8756 -1.4866 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1560 -0.8827 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6667 -3.6581 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.8135 0.4697 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4773 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.4167 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3863 -4.2619 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8135 -0.4697 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.9172 -2.9768 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7839 -3.9794 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8864 -0.8135 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2690 -3.9406 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8864 0.8135 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.3607 -1.4478 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 14 2 0 0 0 0 2 15 1 0 0 0 0 3 22 1 0 0 0 0 4 22 1 0 0 0 0 6 28 1 0 0 0 0 7 10 1 0 0 0 0 7 14 1 0 0 0 0 8 9 1 0 0 0 0 8 16 2 0 0 0 0 9 18 1 0 0 0 0 10 19 1 0 0 0 0 11 12 1 0 0 0 0 11 17 1 0 0 0 0 12 23 1 0 0 0 0 13 16 1 0 0 0 0 13 29 1 0 0 0 0 14 20 1 0 0 0 0 15 24 2 0 0 0 0 15 29 1 0 0 0 0 17 16 1 6 0 0 0 17 20 1 0 0 0 0 18 22 1 0 0 0 0 18 25 1 0 0 0 0 19 23 1 6 0 0 0 19 30 1 0 0 0 0 20 21 1 1 0 0 0 21 26 2 0 0 0 0 21 28 1 0 0 0 0 22 27 1 0 0 0 0 23 5 1 6 0 0 0 23 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	424.25
Volume:	440.237
LogP:	2.689
LogD:	2.323
LogS:	-3.487
# Rotatable Bonds:	9
TPSA:	105.59
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.368
Synthetic Accessibility Score:	4.983
Fsp3:	0.739
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.643
MDCK Permeability:	3.813691364484839e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.631
Human Intestinal Absorption (HIA):	0.569
20% Bioavailability (F20%):	0.953
30% Bioavailability (F30%):	0.991

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.348
Plasma Protein Binding (PPB):	73.96044921875%
Volume Distribution (VD):	0.612
Pgp-substrate:	24.676877975463867%

ADMET: Metabolism

CYP1A2-inhibitor:	0.016
CYP1A2-substrate:	0.108
CYP2C19-inhibitor:	0.047
CYP2C19-substrate:	0.779
CYP2C9-inhibitor:	0.059
CYP2C9-substrate:	0.046
CYP2D6-inhibitor:	0.013
CYP2D6-substrate:	0.087
CYP3A4-inhibitor:	0.476
CYP3A4-substrate:	0.516

ADMET: Excretion

Clearance (CL):	5.297
Half-life (T1/2):	0.615

ADMET: Toxicity

hERG Blockers:	0.019
Human Hepatotoxicity (H-HT):	0.388
Drug-inuced Liver Injury (DILI):	0.215
AMES Toxicity:	0.36
Rat Oral Acute Toxicity:	0.042
Maximum Recommended Daily Dose:	0.954
Skin Sensitization:	0.443
Carcinogencity:	0.715
Eye Corrosion:	0.004
Eye Irritation:	0.025
Respiratory Toxicity:	0.951

Download Data

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

Natural Product: NPC474765

Natural Product ID:	NPC474765
*Common Name:**	Umbellacin H
IUPAC Name:	methyl (1S,5R,6S,9S)-6-[(E)-1-acetyloxy-5,6-dihydroxy-6-methylhept-2-en-2-yl]-9-methyl-4-methylidene-10-oxabicyclo[7.1.0]decane-5-carboxylate
Synonyms:	Umbellacin H
Standard InCHIKey:	URLHJBAPTRSOSU-CUAQSNGHSA-N
Standard InCHI:	InChI=1S/C23H36O7/c1-14-7-10-19-23(5,30-19)12-11-17(20(14)21(26)28-6)16(13-29-15(2)24)8-9-18(25)22(3,4)27/h8,17-20,25,27H,1,7,9-13H2,2-6H3/b16-8-/t17-,18?,19+,20+,23+/m1/s1
SMILES:	COC(=O)[C@H]1C(=C)CC[C@H]2[C@](CC[C@@H]1/C(=CCC(C(O)(C)C)O)/COC(=O)C)(O2)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL481829
PubChem CID:	44575215
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0000346] Dicarboxylic 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
NPO14298	Xenia umbellata	Species	Xeniidae	Eukaryota	n.a.	Formosan soft coral	n.a.	PMID[12502332]
NPO14298	Xenia umbellata	Species	Xeniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[16562830]
NPO14298	Xenia umbellata	Species	Xeniidae	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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	ED50	=	3.4	ug ml-1	PMID[553364]

☑ 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 NPC474765 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	227
0.1-0.2	1353
0.2-0.3	4962
0.3-0.4	12780
0.4-0.5	12381
0.5-0.6	7208
0.6-0.7	3348
0.7-0.8	412
0.8-0.85	20
0.85-0.9	5
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.939	High Similarity	NPC474776
0.9036	High Similarity	NPC475842
0.8989	High Similarity	NPC107476
0.8652	High Similarity	NPC475972
0.8605	High Similarity	NPC137033
0.8602	High Similarity	NPC475053
0.8588	High Similarity	NPC11620
0.8571	High Similarity	NPC272050
0.8539	High Similarity	NPC476004
0.8539	High Similarity	NPC474761
0.8523	High Similarity	NPC281516
0.8506	High Similarity	NPC116575
0.8471	Intermediate Similarity	NPC475936
0.8462	Intermediate Similarity	NPC81386
0.8462	Intermediate Similarity	NPC474035
0.8444	Intermediate Similarity	NPC30515
0.8409	Intermediate Similarity	NPC248602
0.8372	Intermediate Similarity	NPC53867
0.837	Intermediate Similarity	NPC14961
0.837	Intermediate Similarity	NPC270013
0.8352	Intermediate Similarity	NPC212486
0.8333	Intermediate Similarity	NPC51004
0.8315	Intermediate Similarity	NPC153805
0.8315	Intermediate Similarity	NPC474471
0.8315	Intermediate Similarity	NPC202672
0.8315	Intermediate Similarity	NPC227379
0.8313	Intermediate Similarity	NPC84360
0.8295	Intermediate Similarity	NPC164393
0.828	Intermediate Similarity	NPC476315
0.8276	Intermediate Similarity	NPC72464
0.8276	Intermediate Similarity	NPC9868
0.8242	Intermediate Similarity	NPC184463
0.8235	Intermediate Similarity	NPC103634
0.8222	Intermediate Similarity	NPC307411
0.8222	Intermediate Similarity	NPC212598
0.8222	Intermediate Similarity	NPC115179
0.8222	Intermediate Similarity	NPC106040
0.8222	Intermediate Similarity	NPC473564
0.8214	Intermediate Similarity	NPC474341
0.8193	Intermediate Similarity	NPC271070
0.8182	Intermediate Similarity	NPC474547
0.8182	Intermediate Similarity	NPC474369
0.8172	Intermediate Similarity	NPC36954
0.8161	Intermediate Similarity	NPC231601
0.8152	Intermediate Similarity	NPC476049
0.8152	Intermediate Similarity	NPC475912
0.8152	Intermediate Similarity	NPC81419
0.8152	Intermediate Similarity	NPC476300
0.8152	Intermediate Similarity	NPC179746
0.814	Intermediate Similarity	NPC474894
0.8132	Intermediate Similarity	NPC473448
0.8132	Intermediate Similarity	NPC316228
0.809	Intermediate Similarity	NPC122502
0.8072	Intermediate Similarity	NPC475861
0.8068	Intermediate Similarity	NPC243618
0.8068	Intermediate Similarity	NPC70424
0.8046	Intermediate Similarity	NPC474291
0.8043	Intermediate Similarity	NPC12172
0.8043	Intermediate Similarity	NPC208886
0.8	Intermediate Similarity	NPC231889
0.7978	Intermediate Similarity	NPC47958
0.7978	Intermediate Similarity	NPC149725
0.7978	Intermediate Similarity	NPC304509
0.7957	Intermediate Similarity	NPC475838
0.7957	Intermediate Similarity	NPC125674
0.7957	Intermediate Similarity	NPC228451
0.7955	Intermediate Similarity	NPC170377
0.7935	Intermediate Similarity	NPC475748
0.7927	Intermediate Similarity	NPC477084
0.7917	Intermediate Similarity	NPC473326
0.7917	Intermediate Similarity	NPC222303
0.7907	Intermediate Similarity	NPC86971
0.7901	Intermediate Similarity	NPC101622
0.7895	Intermediate Similarity	NPC473291
0.7895	Intermediate Similarity	NPC279621
0.7895	Intermediate Similarity	NPC473859
0.7889	Intermediate Similarity	NPC261253
0.7889	Intermediate Similarity	NPC474045
0.7872	Intermediate Similarity	NPC303942
0.7872	Intermediate Similarity	NPC474247
0.7872	Intermediate Similarity	NPC57405
0.7865	Intermediate Similarity	NPC82297
0.7865	Intermediate Similarity	NPC474780
0.7857	Intermediate Similarity	NPC474709
0.7841	Intermediate Similarity	NPC89555
0.7835	Intermediate Similarity	NPC288876
0.7831	Intermediate Similarity	NPC477085
0.7826	Intermediate Similarity	NPC295312
0.7826	Intermediate Similarity	NPC474032
0.7816	Intermediate Similarity	NPC474739
0.7816	Intermediate Similarity	NPC233377
0.7805	Intermediate Similarity	NPC4299
0.7802	Intermediate Similarity	NPC179659
0.7802	Intermediate Similarity	NPC475703
0.78	Intermediate Similarity	NPC243998
0.7789	Intermediate Similarity	NPC471141
0.7789	Intermediate Similarity	NPC475659
0.7778	Intermediate Similarity	NPC474775
0.7778	Intermediate Similarity	NPC329749
0.7778	Intermediate Similarity	NPC21469
0.7765	Intermediate Similarity	NPC61863
0.7755	Intermediate Similarity	NPC473332
0.7755	Intermediate Similarity	NPC476270
0.7753	Intermediate Similarity	NPC23748
0.7753	Intermediate Similarity	NPC272814
0.7753	Intermediate Similarity	NPC250315
0.7753	Intermediate Similarity	NPC475989
0.7742	Intermediate Similarity	NPC313670
0.7732	Intermediate Similarity	NPC474213
0.7732	Intermediate Similarity	NPC187268
0.7732	Intermediate Similarity	NPC161855
0.7727	Intermediate Similarity	NPC79277
0.7727	Intermediate Similarity	NPC325031
0.7727	Intermediate Similarity	NPC141810
0.7727	Intermediate Similarity	NPC475481
0.7723	Intermediate Similarity	NPC326994
0.7723	Intermediate Similarity	NPC194620
0.7723	Intermediate Similarity	NPC72813
0.7723	Intermediate Similarity	NPC474421
0.7723	Intermediate Similarity	NPC324327
0.7717	Intermediate Similarity	NPC177629
0.7717	Intermediate Similarity	NPC58219
0.7711	Intermediate Similarity	NPC477087
0.7711	Intermediate Similarity	NPC477086
0.7708	Intermediate Similarity	NPC230800
0.7701	Intermediate Similarity	NPC471537
0.7701	Intermediate Similarity	NPC89128
0.77	Intermediate Similarity	NPC474741
0.7692	Intermediate Similarity	NPC470242
0.7692	Intermediate Similarity	NPC469676
0.7692	Intermediate Similarity	NPC475019
0.7692	Intermediate Similarity	NPC50637
0.7692	Intermediate Similarity	NPC474949
0.7684	Intermediate Similarity	NPC71589
0.7683	Intermediate Similarity	NPC269841
0.7677	Intermediate Similarity	NPC471148
0.7674	Intermediate Similarity	NPC107668
0.7674	Intermediate Similarity	NPC40049
0.7667	Intermediate Similarity	NPC186155
0.7667	Intermediate Similarity	NPC78673
0.7667	Intermediate Similarity	NPC160517
0.766	Intermediate Similarity	NPC219874
0.7653	Intermediate Similarity	NPC474718
0.7647	Intermediate Similarity	NPC233379
0.7647	Intermediate Similarity	NPC14862
0.7647	Intermediate Similarity	NPC327286
0.7647	Intermediate Similarity	NPC55972
0.7647	Intermediate Similarity	NPC169888
0.7647	Intermediate Similarity	NPC474664
0.764	Intermediate Similarity	NPC35556
0.7634	Intermediate Similarity	NPC83423
0.7634	Intermediate Similarity	NPC151770
0.7634	Intermediate Similarity	NPC166919
0.7634	Intermediate Similarity	NPC92974
0.7629	Intermediate Similarity	NPC40812
0.7624	Intermediate Similarity	NPC223450
0.7624	Intermediate Similarity	NPC9303
0.7624	Intermediate Similarity	NPC16313
0.7624	Intermediate Similarity	NPC179891
0.7619	Intermediate Similarity	NPC135703
0.7614	Intermediate Similarity	NPC474510
0.7609	Intermediate Similarity	NPC186148
0.7609	Intermediate Similarity	NPC477959
0.7609	Intermediate Similarity	NPC160138
0.7609	Intermediate Similarity	NPC471738
0.7604	Intermediate Similarity	NPC472469
0.7604	Intermediate Similarity	NPC304886
0.76	Intermediate Similarity	NPC4620
0.76	Intermediate Similarity	NPC69171
0.76	Intermediate Similarity	NPC474165
0.76	Intermediate Similarity	NPC475871
0.76	Intermediate Similarity	NPC475945
0.759	Intermediate Similarity	NPC475310
0.7586	Intermediate Similarity	NPC477089
0.7582	Intermediate Similarity	NPC99395
0.7582	Intermediate Similarity	NPC255307
0.7582	Intermediate Similarity	NPC471494
0.7582	Intermediate Similarity	NPC197903
0.7582	Intermediate Similarity	NPC261380
0.7579	Intermediate Similarity	NPC320089
0.7576	Intermediate Similarity	NPC150923
0.7576	Intermediate Similarity	NPC474742
0.7576	Intermediate Similarity	NPC472753
0.7576	Intermediate Similarity	NPC474339
0.7576	Intermediate Similarity	NPC164598
0.7573	Intermediate Similarity	NPC15218
0.7573	Intermediate Similarity	NPC475922
0.7558	Intermediate Similarity	NPC301525
0.7558	Intermediate Similarity	NPC12740
0.7558	Intermediate Similarity	NPC110461
0.7556	Intermediate Similarity	NPC49208
0.7556	Intermediate Similarity	NPC1761
0.7556	Intermediate Similarity	NPC52609
0.7553	Intermediate Similarity	NPC469368
0.7553	Intermediate Similarity	NPC473619
0.7553	Intermediate Similarity	NPC475855
0.7553	Intermediate Similarity	NPC3952
0.7553	Intermediate Similarity	NPC62815
0.7551	Intermediate Similarity	NPC83895
0.7551	Intermediate Similarity	NPC187761

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 NPC474765 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	226
0.1-0.2	2043
0.2-0.3	3650
0.3-0.4	2177
0.4-0.5	747
0.5-0.6	253
0.6-0.7	45
0.7-0.8	9
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
0.8333	Intermediate Similarity	NPD46	Approved
0.8333	Intermediate Similarity	NPD6698	Approved
0.7742	Intermediate Similarity	NPD7838	Discovery
0.766	Intermediate Similarity	NPD7983	Approved
0.7396	Intermediate Similarity	NPD5779	Approved
0.7396	Intermediate Similarity	NPD5778	Approved
0.7391	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7363	Intermediate Similarity	NPD7154	Phase 3
0.7363	Intermediate Similarity	NPD5362	Discontinued
0.7333	Intermediate Similarity	NPD6371	Approved
0.7228	Intermediate Similarity	NPD5344	Discontinued
0.7212	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5369	Approved
0.7128	Intermediate Similarity	NPD5786	Approved
0.7083	Intermediate Similarity	NPD6101	Approved
0.7083	Intermediate Similarity	NPD1695	Approved
0.7083	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD4270	Approved
0.7065	Intermediate Similarity	NPD6435	Approved
0.7065	Intermediate Similarity	NPD4269	Approved
0.7033	Intermediate Similarity	NPD4820	Approved
0.7033	Intermediate Similarity	NPD5790	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD4819	Approved
0.7033	Intermediate Similarity	NPD4821	Approved
0.7033	Intermediate Similarity	NPD4822	Approved
0.7021	Intermediate Similarity	NPD6082	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD5785	Approved
0.7	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD6686	Approved
0.6944	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD6411	Approved
0.69	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD6053	Discontinued
0.6875	Remote Similarity	NPD4250	Approved
0.6875	Remote Similarity	NPD4251	Approved
0.6863	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD7638	Approved
0.6848	Remote Similarity	NPD5368	Approved
0.6848	Remote Similarity	NPD4252	Approved
0.6842	Remote Similarity	NPD5363	Approved
0.6832	Remote Similarity	NPD7839	Suspended
0.6813	Remote Similarity	NPD4268	Approved
0.6813	Remote Similarity	NPD4271	Approved
0.6809	Remote Similarity	NPD5332	Approved
0.6809	Remote Similarity	NPD5331	Approved
0.6796	Remote Similarity	NPD6648	Approved
0.6796	Remote Similarity	NPD7639	Approved
0.6796	Remote Similarity	NPD7640	Approved
0.6786	Remote Similarity	NPD7115	Discovery
0.6774	Remote Similarity	NPD4790	Discontinued
0.6771	Remote Similarity	NPD4249	Approved
0.6759	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD4225	Approved
0.6667	Remote Similarity	NPD3197	Phase 1
0.6667	Remote Similarity	NPD8039	Approved
0.6552	Remote Similarity	NPD8517	Approved
0.6552	Remote Similarity	NPD8515	Approved
0.6552	Remote Similarity	NPD8513	Phase 3
0.6552	Remote Similarity	NPD8516	Approved
0.6535	Remote Similarity	NPD6399	Phase 3
0.6471	Remote Similarity	NPD8273	Phase 1
0.6471	Remote Similarity	NPD7909	Approved
0.6458	Remote Similarity	NPD6110	Phase 1
0.6437	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD7637	Suspended
0.6429	Remote Similarity	NPD6422	Discontinued
0.6396	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6354	Remote Similarity	NPD5209	Approved
0.6333	Remote Similarity	NPD7507	Approved
0.6327	Remote Similarity	NPD1694	Approved
0.6322	Remote Similarity	NPD7331	Phase 2
0.6311	Remote Similarity	NPD7748	Approved
0.6311	Remote Similarity	NPD5282	Discontinued
0.6303	Remote Similarity	NPD7829	Approved
0.6303	Remote Similarity	NPD7642	Approved
0.6303	Remote Similarity	NPD7830	Approved
0.6286	Remote Similarity	NPD6084	Phase 2
0.6286	Remote Similarity	NPD6083	Phase 2
0.6281	Remote Similarity	NPD8074	Phase 3
0.6275	Remote Similarity	NPD7515	Phase 2
0.6238	Remote Similarity	NPD5370	Suspended
0.6224	Remote Similarity	NPD4786	Approved
0.6224	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD7341	Phase 2
0.6204	Remote Similarity	NPD7632	Discontinued
0.62	Remote Similarity	NPD7524	Approved
0.6198	Remote Similarity	NPD8451	Approved
0.619	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD3667	Approved
0.6186	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6182	Remote Similarity	NPD7128	Approved
0.6182	Remote Similarity	NPD6675	Approved
0.6182	Remote Similarity	NPD5739	Approved
0.6182	Remote Similarity	NPD6402	Approved
0.6182	Remote Similarity	NPD6008	Approved
0.6179	Remote Similarity	NPD7319	Approved
0.6148	Remote Similarity	NPD8448	Approved
0.6134	Remote Similarity	NPD8444	Approved
0.6132	Remote Similarity	NPD7902	Approved
0.6126	Remote Similarity	NPD6412	Phase 2
0.6126	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6122	Remote Similarity	NPD6695	Phase 3
0.6118	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6117	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.61	Remote Similarity	NPD7146	Approved
0.61	Remote Similarity	NPD6409	Approved
0.61	Remote Similarity	NPD7334	Approved
0.61	Remote Similarity	NPD7521	Approved
0.61	Remote Similarity	NPD5330	Approved
0.61	Remote Similarity	NPD6684	Approved
0.6095	Remote Similarity	NPD5695	Phase 3
0.6087	Remote Similarity	NPD4632	Approved
0.6087	Remote Similarity	NPD8133	Approved
0.6078	Remote Similarity	NPD6051	Approved
0.6071	Remote Similarity	NPD7320	Approved
0.6071	Remote Similarity	NPD6899	Approved
0.6071	Remote Similarity	NPD6881	Approved
0.6064	Remote Similarity	NPD6933	Approved
0.6061	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6018	Remote Similarity	NPD6373	Approved
0.6018	Remote Similarity	NPD6372	Approved
0.6	Remote Similarity	NPD4756	Discovery
0.6	Remote Similarity	NPD8392	Approved
0.6	Remote Similarity	NPD8391	Approved
0.6	Remote Similarity	NPD8390	Approved
0.6	Remote Similarity	NPD8297	Approved
0.5984	Remote Similarity	NPD8341	Approved
0.5984	Remote Similarity	NPD8340	Approved
0.5984	Remote Similarity	NPD8299	Approved
0.5984	Remote Similarity	NPD8342	Approved
0.5982	Remote Similarity	NPD5701	Approved
0.5982	Remote Similarity	NPD5697	Approved
0.598	Remote Similarity	NPD6672	Approved
0.598	Remote Similarity	NPD5737	Approved
0.598	Remote Similarity	NPD6903	Approved
0.598	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5976	Remote Similarity	NPD3196	Approved
0.5976	Remote Similarity	NPD3195	Phase 2
0.5976	Remote Similarity	NPD4266	Approved
0.5976	Remote Similarity	NPD3194	Approved
0.5965	Remote Similarity	NPD7102	Approved
0.5965	Remote Similarity	NPD6421	Discontinued
0.5965	Remote Similarity	NPD7290	Approved
0.5965	Remote Similarity	NPD6883	Approved
0.5962	Remote Similarity	NPD5693	Phase 1
0.5929	Remote Similarity	NPD6011	Approved
0.5926	Remote Similarity	NPD5696	Approved
0.5922	Remote Similarity	NPD5328	Approved
0.5917	Remote Similarity	NPD6319	Approved
0.5913	Remote Similarity	NPD6649	Approved
0.5913	Remote Similarity	NPD6650	Approved
0.5913	Remote Similarity	NPD6617	Approved
0.5913	Remote Similarity	NPD6869	Approved
0.5913	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5913	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.5913	Remote Similarity	NPD8130	Phase 1
0.5913	Remote Similarity	NPD2204	Approved
0.5913	Remote Similarity	NPD6847	Approved
0.5902	Remote Similarity	NPD7604	Phase 2
0.59	Remote Similarity	NPD3666	Approved
0.59	Remote Similarity	NPD3133	Approved
0.59	Remote Similarity	NPD3665	Phase 1
0.5882	Remote Similarity	NPD7750	Discontinued
0.5882	Remote Similarity	NPD7641	Discontinued
0.5882	Remote Similarity	NPD7327	Approved
0.5882	Remote Similarity	NPD7328	Approved
0.5877	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.5877	Remote Similarity	NPD6013	Approved
0.5877	Remote Similarity	NPD6012	Approved
0.5877	Remote Similarity	NPD6014	Approved
0.5868	Remote Similarity	NPD8033	Approved
0.5865	Remote Similarity	NPD3168	Discontinued
0.5862	Remote Similarity	NPD368	Approved
0.5862	Remote Similarity	NPD6882	Approved
0.5854	Remote Similarity	NPD3172	Approved
0.5851	Remote Similarity	NPD6924	Approved
0.5851	Remote Similarity	NPD6926	Approved
0.5849	Remote Similarity	NPD7900	Approved
0.5849	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5846	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.5842	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD7516	Approved
0.5827	Remote Similarity	NPD7260	Phase 2
0.5826	Remote Similarity	NPD6420	Discontinued
0.5816	Remote Similarity	NPD4695	Discontinued
0.5816	Remote Similarity	NPD6931	Approved
0.5816	Remote Similarity	NPD6930	Phase 2
0.5814	Remote Similarity	NPD3198	Approved
0.581	Remote Similarity	NPD6079	Approved
0.581	Remote Similarity	NPD8035	Phase 2
0.581	Remote Similarity	NPD8034	Phase 2
0.5802	Remote Similarity	NPD6927	Phase 3
0.5798	Remote Similarity	NPD6009	Approved
0.5798	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.5798	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.5794	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5785	Remote Similarity	NPD8294	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