NPASS Compound

Structure

NPC475972 OpenBabel07101718202D 30 31 0 0 1 0 0 0 0 0999 V2000 5.0575 0.9088 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2915 6.2325 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2943 6.1578 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4110 -0.9116 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9902 3.2738 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0151 1.4888 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2798 3.2077 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1061 3.7710 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2514 0.7225 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6774 0.6583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9972 -0.0747 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5633 0.8262 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2555 1.7766 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9827 1.9060 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2686 1.7818 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3546 2.2105 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5283 1.6472 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.0314 4.7682 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.7997 0.0599 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6623 2.1472 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7370 3.1444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8576 5.3315 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.8090 2.4693 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1304 5.2021 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2997 -0.8061 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6380 3.5782 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7586 4.8976 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0892 3.7077 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0818 2.3399 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 1 0 0 0 0 2 22 1 0 0 0 0 3 22 1 0 0 0 0 5 29 1 0 0 0 0 6 9 1 0 0 0 0 6 15 2 0 0 0 0 7 8 1 0 0 0 0 7 16 2 0 0 0 0 8 18 1 0 0 0 0 9 19 1 0 0 0 0 10 11 1 0 0 0 0 10 17 1 0 0 0 0 11 23 1 0 0 0 0 12 15 1 0 0 0 0 12 23 1 0 0 0 0 13 16 1 0 0 0 0 13 30 1 0 0 0 0 14 24 2 0 0 0 0 14 30 1 0 0 0 0 15 20 1 0 0 0 0 17 16 1 1 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 26 1 0 0 0 0 20 21 1 6 0 0 0 21 27 2 0 0 0 0 21 29 1 0 0 0 0 22 28 1 0 0 0 0 23 4 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	424.25
Volume:	440.237
LogP:	1.503
LogD:	1.351
LogS:	-2.682
# Rotatable Bonds:	9
TPSA:	113.29
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.425
Synthetic Accessibility Score:	5.337
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:	-4.99
MDCK Permeability:	4.8083424189826474e-05
Pgp-inhibitor:	0.938
Pgp-substrate:	0.971
Human Intestinal Absorption (HIA):	0.92
20% Bioavailability (F20%):	0.992
30% Bioavailability (F30%):	0.964

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.284
Plasma Protein Binding (PPB):	75.91838073730469%
Volume Distribution (VD):	0.387
Pgp-substrate:	22.565940856933594%

ADMET: Metabolism

CYP1A2-inhibitor:	0.021
CYP1A2-substrate:	0.1
CYP2C19-inhibitor:	0.026
CYP2C19-substrate:	0.643
CYP2C9-inhibitor:	0.035
CYP2C9-substrate:	0.113
CYP2D6-inhibitor:	0.01
CYP2D6-substrate:	0.066
CYP3A4-inhibitor:	0.367
CYP3A4-substrate:	0.342

ADMET: Excretion

Clearance (CL):	2.721
Half-life (T1/2):	0.627

ADMET: Toxicity

hERG Blockers:	0.008
Human Hepatotoxicity (H-HT):	0.211
Drug-inuced Liver Injury (DILI):	0.109
AMES Toxicity:	0.056
Rat Oral Acute Toxicity:	0.024
Maximum Recommended Daily Dose:	0.976
Skin Sensitization:	0.233
Carcinogencity:	0.768
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.952

Download Data

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

Natural Product: NPC475972

Natural Product ID:	NPC475972
*Common Name:**	Umbellacin E
IUPAC Name:	methyl (2R,3S,6S,7R)-3-[(E)-1-acetyloxy-5,6-dihydroxy-6-methylhept-2-en-2-yl]-7-hydroxy-6-methylbicyclo[4.3.1]dec-1(9)-ene-2-carboxylate
Synonyms:	Umbellacin E
Standard InCHIKey:	SKUXBRSPQCLBOB-UIVDZBMSSA-N
Standard InCHI:	InChI=1S/C23H36O7/c1-14(24)30-13-16(7-8-18(25)22(2,3)28)17-10-11-23(4)12-15(6-9-19(23)26)20(17)21(27)29-5/h6-7,17-20,25-26,28H,8-13H2,1-5H3/b16-7-/t17-,18?,19-,20+,23+/m1/s1
SMILES:	COC(=O)[C@H]1C2=CC[C@H]([C@](C2)(CC[C@@H]1/C(=CCC(C(O)(C)C)O)/COC(=O)C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL519958
PubChem CID:	11683278
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	=	3.8	ug ml-1	PMID[497057]

☑ 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 NPC475972 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	216
0.1-0.2	1216
0.2-0.3	4490
0.3-0.4	10829
0.4-0.5	12783
0.5-0.6	6868
0.6-0.7	5444
0.7-0.8	830
0.8-0.85	15
0.85-0.9	5
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8842	High Similarity	NPC474709
0.8736	High Similarity	NPC474776
0.8652	High Similarity	NPC474765
0.8632	High Similarity	NPC474718
0.8367	Intermediate Similarity	NPC474165
0.8367	Intermediate Similarity	NPC69171
0.8298	Intermediate Similarity	NPC470957
0.8298	Intermediate Similarity	NPC470958
0.8265	Intermediate Similarity	NPC183571
0.8265	Intermediate Similarity	NPC478156
0.8242	Intermediate Similarity	NPC248602
0.8229	Intermediate Similarity	NPC285513
0.8229	Intermediate Similarity	NPC254496
0.8222	Intermediate Similarity	NPC137033
0.8202	Intermediate Similarity	NPC11620
0.8202	Intermediate Similarity	NPC23748
0.82	Intermediate Similarity	NPC127609
0.8182	Intermediate Similarity	NPC474775
0.8172	Intermediate Similarity	NPC476004
0.8172	Intermediate Similarity	NPC474761
0.8152	Intermediate Similarity	NPC153805
0.8152	Intermediate Similarity	NPC227379
0.8152	Intermediate Similarity	NPC474471
0.8144	Intermediate Similarity	NPC222303
0.8111	Intermediate Similarity	NPC9868
0.8105	Intermediate Similarity	NPC250075
0.81	Intermediate Similarity	NPC239162
0.8085	Intermediate Similarity	NPC30515
0.8068	Intermediate Similarity	NPC103634
0.8043	Intermediate Similarity	NPC312561
0.8041	Intermediate Similarity	NPC474977
0.8021	Intermediate Similarity	NPC134067
0.8021	Intermediate Similarity	NPC272050
0.8	Intermediate Similarity	NPC4620
0.8	Intermediate Similarity	NPC475321
0.8	Intermediate Similarity	NPC49208
0.8	Intermediate Similarity	NPC99266
0.798	Intermediate Similarity	NPC471412
0.7979	Intermediate Similarity	NPC51004
0.7979	Intermediate Similarity	NPC232426
0.7979	Intermediate Similarity	NPC232202
0.7979	Intermediate Similarity	NPC281942
0.7978	Intermediate Similarity	NPC229584
0.7978	Intermediate Similarity	NPC14203
0.7961	Intermediate Similarity	NPC475922
0.7957	Intermediate Similarity	NPC281516
0.7957	Intermediate Similarity	NPC202672
0.7935	Intermediate Similarity	NPC116575
0.7935	Intermediate Similarity	NPC164393
0.7921	Intermediate Similarity	NPC475676
0.7921	Intermediate Similarity	NPC220964
0.7921	Intermediate Similarity	NPC258532
0.7912	Intermediate Similarity	NPC70424
0.7912	Intermediate Similarity	NPC243618
0.79	Intermediate Similarity	NPC475091
0.79	Intermediate Similarity	NPC137430
0.79	Intermediate Similarity	NPC475320
0.7895	Intermediate Similarity	NPC141831
0.7895	Intermediate Similarity	NPC303697
0.7895	Intermediate Similarity	NPC477574
0.7895	Intermediate Similarity	NPC184463
0.7889	Intermediate Similarity	NPC474291
0.7885	Intermediate Similarity	NPC161816
0.7885	Intermediate Similarity	NPC115257
0.7879	Intermediate Similarity	NPC471413
0.7872	Intermediate Similarity	NPC20946
0.7872	Intermediate Similarity	NPC246028
0.7872	Intermediate Similarity	NPC307411
0.7864	Intermediate Similarity	NPC151393
0.7857	Intermediate Similarity	NPC69385
0.7849	Intermediate Similarity	NPC477926
0.7843	Intermediate Similarity	NPC179891
0.7835	Intermediate Similarity	NPC53565
0.7835	Intermediate Similarity	NPC36954
0.7835	Intermediate Similarity	NPC107476
0.783	Intermediate Similarity	NPC311592
0.783	Intermediate Similarity	NPC75167
0.7822	Intermediate Similarity	NPC8196
0.7822	Intermediate Similarity	NPC36688
0.7812	Intermediate Similarity	NPC99653
0.7812	Intermediate Similarity	NPC81419
0.7812	Intermediate Similarity	NPC476300
0.7812	Intermediate Similarity	NPC475912
0.7812	Intermediate Similarity	NPC179746
0.7812	Intermediate Similarity	NPC476049
0.781	Intermediate Similarity	NPC324683
0.7802	Intermediate Similarity	NPC475842
0.78	Intermediate Similarity	NPC97435
0.78	Intermediate Similarity	NPC303559
0.7789	Intermediate Similarity	NPC316228
0.7789	Intermediate Similarity	NPC158488
0.7789	Intermediate Similarity	NPC214844
0.7789	Intermediate Similarity	NPC473448
0.7788	Intermediate Similarity	NPC472216
0.7788	Intermediate Similarity	NPC5475
0.7788	Intermediate Similarity	NPC42662
0.7788	Intermediate Similarity	NPC284828
0.7788	Intermediate Similarity	NPC273433
0.7788	Intermediate Similarity	NPC173905
0.7778	Intermediate Similarity	NPC222011
0.7778	Intermediate Similarity	NPC23364
0.7778	Intermediate Similarity	NPC327002
0.7778	Intermediate Similarity	NPC134430
0.7767	Intermediate Similarity	NPC474421
0.7767	Intermediate Similarity	NPC324327
0.7767	Intermediate Similarity	NPC326994
0.7767	Intermediate Similarity	NPC301666
0.7767	Intermediate Similarity	NPC72813
0.7767	Intermediate Similarity	NPC67321
0.7767	Intermediate Similarity	NPC194620
0.7767	Intermediate Similarity	NPC187435
0.7766	Intermediate Similarity	NPC24816
0.7757	Intermediate Similarity	NPC181145
0.7755	Intermediate Similarity	NPC202833
0.7755	Intermediate Similarity	NPC21302
0.7755	Intermediate Similarity	NPC11396
0.7745	Intermediate Similarity	NPC118911
0.7745	Intermediate Similarity	NPC470104
0.7745	Intermediate Similarity	NPC203659
0.7742	Intermediate Similarity	NPC473226
0.7742	Intermediate Similarity	NPC73038
0.7742	Intermediate Similarity	NPC220478
0.7742	Intermediate Similarity	NPC324063
0.7742	Intermediate Similarity	NPC202394
0.7736	Intermediate Similarity	NPC476801
0.7736	Intermediate Similarity	NPC277769
0.7732	Intermediate Similarity	NPC91010
0.7732	Intermediate Similarity	NPC476415
0.7732	Intermediate Similarity	NPC474035
0.7732	Intermediate Similarity	NPC65829
0.7732	Intermediate Similarity	NPC469491
0.7732	Intermediate Similarity	NPC53685
0.7732	Intermediate Similarity	NPC81386
0.7727	Intermediate Similarity	NPC40049
0.7723	Intermediate Similarity	NPC295791
0.7723	Intermediate Similarity	NPC476081
0.7723	Intermediate Similarity	NPC31058
0.7723	Intermediate Similarity	NPC469606
0.7723	Intermediate Similarity	NPC162973
0.7723	Intermediate Similarity	NPC273005
0.7717	Intermediate Similarity	NPC72464
0.7717	Intermediate Similarity	NPC295799
0.7714	Intermediate Similarity	NPC472215
0.7714	Intermediate Similarity	NPC475563
0.7714	Intermediate Similarity	NPC475134
0.7714	Intermediate Similarity	NPC5103
0.7714	Intermediate Similarity	NPC83005
0.7714	Intermediate Similarity	NPC472214
0.7708	Intermediate Similarity	NPC208886
0.7708	Intermediate Similarity	NPC234335
0.7708	Intermediate Similarity	NPC12172
0.7708	Intermediate Similarity	NPC124374
0.77	Intermediate Similarity	NPC241221
0.77	Intermediate Similarity	NPC54705
0.77	Intermediate Similarity	NPC475053
0.7692	Intermediate Similarity	NPC308191
0.7692	Intermediate Similarity	NPC94377
0.7692	Intermediate Similarity	NPC327286
0.7692	Intermediate Similarity	NPC472218
0.7692	Intermediate Similarity	NPC306265
0.7692	Intermediate Similarity	NPC275539
0.7692	Intermediate Similarity	NPC169888
0.7692	Intermediate Similarity	NPC189075
0.7692	Intermediate Similarity	NPC233379
0.7692	Intermediate Similarity	NPC89555
0.7692	Intermediate Similarity	NPC474664
0.7692	Intermediate Similarity	NPC14862
0.7692	Intermediate Similarity	NPC89171
0.7692	Intermediate Similarity	NPC472219
0.7692	Intermediate Similarity	NPC476802
0.7692	Intermediate Similarity	NPC472217
0.7692	Intermediate Similarity	NPC55972
0.7692	Intermediate Similarity	NPC476479
0.7684	Intermediate Similarity	NPC212598
0.7684	Intermediate Similarity	NPC261320
0.7684	Intermediate Similarity	NPC5509
0.7684	Intermediate Similarity	NPC473564
0.7677	Intermediate Similarity	NPC134454
0.7677	Intermediate Similarity	NPC17326
0.7677	Intermediate Similarity	NPC474343
0.767	Intermediate Similarity	NPC173172
0.767	Intermediate Similarity	NPC9303
0.767	Intermediate Similarity	NPC475414
0.767	Intermediate Similarity	NPC469607
0.767	Intermediate Similarity	NPC111952
0.767	Intermediate Similarity	NPC16313
0.7667	Intermediate Similarity	NPC233377
0.7664	Intermediate Similarity	NPC469463
0.7664	Intermediate Similarity	NPC471204
0.7664	Intermediate Similarity	NPC469496
0.7664	Intermediate Similarity	NPC469454
0.766	Intermediate Similarity	NPC245004
0.766	Intermediate Similarity	NPC131329
0.7653	Intermediate Similarity	NPC472469
0.7653	Intermediate Similarity	NPC14961
0.7653	Intermediate Similarity	NPC270013
0.7653	Intermediate Similarity	NPC304886
0.7653	Intermediate Similarity	NPC37603
0.7653	Intermediate Similarity	NPC471786
0.7653	Intermediate Similarity	NPC183012

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 NPC475972 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	195
0.1-0.2	1814
0.2-0.3	3609
0.3-0.4	2321
0.4-0.5	775
0.5-0.6	352
0.6-0.7	71
0.7-0.8	13
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
0.7789	Intermediate Similarity	NPD6698	Approved
0.7789	Intermediate Similarity	NPD46	Approved
0.7547	Intermediate Similarity	NPD6371	Approved
0.7449	Intermediate Similarity	NPD5779	Approved
0.7449	Intermediate Similarity	NPD5778	Approved
0.7426	Intermediate Similarity	NPD7638	Approved
0.7358	Intermediate Similarity	NPD6686	Approved
0.7353	Intermediate Similarity	NPD7640	Approved
0.7353	Intermediate Similarity	NPD7639	Approved
0.7347	Intermediate Similarity	NPD6411	Approved
0.7347	Intermediate Similarity	NPD7983	Approved
0.73	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6399	Phase 3
0.7264	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD4225	Approved
0.7248	Intermediate Similarity	NPD6053	Discontinued
0.7143	Intermediate Similarity	NPD6101	Approved
0.7143	Intermediate Similarity	NPD7115	Discovery
0.7143	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD8039	Approved
0.7071	Intermediate Similarity	NPD7838	Discovery
0.7071	Intermediate Similarity	NPD5785	Approved
0.7065	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD5362	Discontinued
0.7053	Intermediate Similarity	NPD7154	Phase 3
0.703	Intermediate Similarity	NPD7748	Approved
0.7	Intermediate Similarity	NPD7515	Phase 2
0.6979	Remote Similarity	NPD4786	Approved
0.6952	Remote Similarity	NPD5344	Discontinued
0.6947	Remote Similarity	NPD3667	Approved
0.6881	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD6675	Approved
0.6852	Remote Similarity	NPD6402	Approved
0.6852	Remote Similarity	NPD7128	Approved
0.6852	Remote Similarity	NPD5739	Approved
0.6847	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD5369	Approved
0.6837	Remote Similarity	NPD5786	Approved
0.6827	Remote Similarity	NPD7902	Approved
0.6827	Remote Similarity	NPD6083	Phase 2
0.6827	Remote Similarity	NPD6084	Phase 2
0.6807	Remote Similarity	NPD7507	Approved
0.68	Remote Similarity	NPD1695	Approved
0.6771	Remote Similarity	NPD4270	Approved
0.6771	Remote Similarity	NPD4269	Approved
0.6771	Remote Similarity	NPD6435	Approved
0.6762	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD8516	Approved
0.6752	Remote Similarity	NPD8517	Approved
0.6752	Remote Similarity	NPD8515	Approved
0.6752	Remote Similarity	NPD8513	Phase 3
0.6737	Remote Similarity	NPD4819	Approved
0.6737	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD4821	Approved
0.6737	Remote Similarity	NPD4822	Approved
0.6737	Remote Similarity	NPD4820	Approved
0.6735	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD1694	Approved
0.6731	Remote Similarity	NPD7839	Suspended
0.6729	Remote Similarity	NPD7632	Discontinued
0.6727	Remote Similarity	NPD6881	Approved
0.6727	Remote Similarity	NPD6899	Approved
0.6727	Remote Similarity	NPD7320	Approved
0.6726	Remote Similarity	NPD4632	Approved
0.6667	Remote Similarity	NPD7521	Approved
0.6667	Remote Similarity	NPD6372	Approved
0.6667	Remote Similarity	NPD7146	Approved
0.6667	Remote Similarity	NPD5330	Approved
0.6667	Remote Similarity	NPD6373	Approved
0.6667	Remote Similarity	NPD7334	Approved
0.6667	Remote Similarity	NPD6684	Approved
0.6667	Remote Similarity	NPD6409	Approved
0.6667	Remote Similarity	NPD7637	Suspended
0.6639	Remote Similarity	NPD7319	Approved
0.6637	Remote Similarity	NPD8297	Approved
0.6636	Remote Similarity	NPD5697	Approved
0.6636	Remote Similarity	NPD5701	Approved
0.6636	Remote Similarity	NPD6412	Phase 2
0.6635	Remote Similarity	NPD5695	Phase 3
0.6634	Remote Similarity	NPD6051	Approved
0.6634	Remote Similarity	NPD5328	Approved
0.6633	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD7290	Approved
0.6607	Remote Similarity	NPD7102	Approved
0.6607	Remote Similarity	NPD6883	Approved
0.66	Remote Similarity	NPD4250	Approved
0.66	Remote Similarity	NPD4251	Approved
0.6579	Remote Similarity	NPD8133	Approved
0.6577	Remote Similarity	NPD6011	Approved
0.6566	Remote Similarity	NPD5363	Approved
0.6562	Remote Similarity	NPD4252	Approved
0.6562	Remote Similarity	NPD5368	Approved
0.6549	Remote Similarity	NPD6847	Approved
0.6549	Remote Similarity	NPD6649	Approved
0.6549	Remote Similarity	NPD6650	Approved
0.6549	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD8130	Phase 1
0.6549	Remote Similarity	NPD6869	Approved
0.6549	Remote Similarity	NPD6617	Approved
0.6545	Remote Similarity	NPD6008	Approved
0.6542	Remote Similarity	NPD6648	Approved
0.6538	Remote Similarity	NPD5282	Discontinued
0.6538	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD7900	Approved
0.6535	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD6672	Approved
0.6535	Remote Similarity	NPD6903	Approved
0.6535	Remote Similarity	NPD5737	Approved
0.6531	Remote Similarity	NPD5331	Approved
0.6531	Remote Similarity	NPD6110	Phase 1
0.6531	Remote Similarity	NPD5332	Approved
0.6526	Remote Similarity	NPD4271	Approved
0.6526	Remote Similarity	NPD4268	Approved
0.6525	Remote Similarity	NPD6319	Approved
0.6518	Remote Similarity	NPD6013	Approved
0.6518	Remote Similarity	NPD6012	Approved
0.6518	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6518	Remote Similarity	NPD6014	Approved
0.6505	Remote Similarity	NPD6079	Approved
0.6505	Remote Similarity	NPD5693	Phase 1
0.65	Remote Similarity	NPD3618	Phase 1
0.65	Remote Similarity	NPD4249	Approved
0.6495	Remote Similarity	NPD4790	Discontinued
0.6491	Remote Similarity	NPD6882	Approved
0.6486	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6475	Remote Similarity	NPD8074	Phase 3
0.6465	Remote Similarity	NPD3668	Phase 3
0.6465	Remote Similarity	NPD3665	Phase 1
0.6465	Remote Similarity	NPD3666	Approved
0.6465	Remote Similarity	NPD3133	Approved
0.6449	Remote Similarity	NPD5696	Approved
0.6436	Remote Similarity	NPD3573	Approved
0.6436	Remote Similarity	NPD7524	Approved
0.641	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.641	Remote Similarity	NPD6009	Approved
0.6404	Remote Similarity	NPD7331	Phase 2
0.64	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6393	Remote Similarity	NPD8273	Phase 1
0.6392	Remote Similarity	NPD4695	Discontinued
0.6383	Remote Similarity	NPD8264	Approved
0.6364	Remote Similarity	NPD7604	Phase 2
0.6364	Remote Similarity	NPD3197	Phase 1
0.6364	Remote Similarity	NPD6695	Phase 3
0.6364	Remote Similarity	NPD8328	Phase 3
0.6356	Remote Similarity	NPD7328	Approved
0.6356	Remote Similarity	NPD7327	Approved
0.6355	Remote Similarity	NPD4755	Approved
0.6346	Remote Similarity	NPD8034	Phase 2
0.6346	Remote Similarity	NPD8035	Phase 2
0.6337	Remote Similarity	NPD5279	Phase 3
0.6337	Remote Similarity	NPD6098	Approved
0.6337	Remote Similarity	NPD6422	Discontinued
0.6333	Remote Similarity	NPD5983	Phase 2
0.6333	Remote Similarity	NPD8033	Approved
0.6316	Remote Similarity	NPD6933	Approved
0.6311	Remote Similarity	NPD6673	Approved
0.6311	Remote Similarity	NPD4753	Phase 2
0.6311	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD7492	Approved
0.6311	Remote Similarity	NPD6080	Approved
0.6311	Remote Similarity	NPD6904	Approved
0.6303	Remote Similarity	NPD7516	Approved
0.63	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6292	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6292	Remote Similarity	NPD7341	Phase 2
0.6286	Remote Similarity	NPD4202	Approved
0.6273	Remote Similarity	NPD5211	Phase 2
0.627	Remote Similarity	NPD7260	Phase 2
0.6263	Remote Similarity	NPD5209	Approved
0.6262	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD5222	Approved
0.6262	Remote Similarity	NPD4697	Phase 3
0.6262	Remote Similarity	NPD5221	Approved
0.626	Remote Similarity	NPD6336	Discontinued
0.626	Remote Similarity	NPD6616	Approved
0.625	Remote Similarity	NPD6059	Approved
0.625	Remote Similarity	NPD8294	Approved
0.625	Remote Similarity	NPD8377	Approved
0.625	Remote Similarity	NPD6054	Approved
0.6239	Remote Similarity	NPD5286	Approved
0.6239	Remote Similarity	NPD4700	Approved
0.6239	Remote Similarity	NPD4696	Approved
0.6239	Remote Similarity	NPD5285	Approved
0.6238	Remote Similarity	NPD1696	Phase 3
0.6224	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6218	Remote Similarity	NPD6335	Approved
0.6211	Remote Similarity	NPD6942	Approved
0.6211	Remote Similarity	NPD7339	Approved
0.621	Remote Similarity	NPD7078	Approved
0.621	Remote Similarity	NPD8293	Discontinued
0.6204	Remote Similarity	NPD5173	Approved
0.6198	Remote Similarity	NPD8335	Approved
0.6198	Remote Similarity	NPD8296	Approved
0.6198	Remote Similarity	NPD8380	Approved
0.6198	Remote Similarity	NPD8379	Approved
0.6198	Remote Similarity	NPD8378	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