NPASS Compound

Structure

NPC473436 OpenBabel07101718222D 31 35 0 0 1 0 0 0 0 0999 V2000 6.1235 -5.1270 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7707 -4.5917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1527 -2.6896 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1890 -4.5032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1913 -3.4135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5054 -3.2248 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8363 -3.9680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1369 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7926 -4.3838 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4836 -3.4328 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8581 -3.7601 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5491 -2.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 2 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 -2.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2990 -0.2500 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 17 1 0 0 0 0 2 17 1 0 0 0 0 3 18 2 0 0 0 0 6 7 1 0 0 0 0 6 18 1 0 0 0 0 7 19 1 0 0 0 0 8 9 1 0 0 0 0 8 22 1 0 0 0 0 9 23 1 0 0 0 0 10 13 1 0 0 0 0 10 20 1 0 0 0 0 11 12 1 0 0 0 0 11 24 1 0 0 0 0 12 26 1 0 0 0 0 13 27 1 0 0 0 0 14 25 1 0 0 0 0 15 20 1 0 0 0 0 15 28 1 0 0 0 0 16 27 1 0 0 0 0 16 31 1 0 0 0 0 17 18 1 0 0 0 0 19 4 1 1 0 0 0 19 22 1 0 0 0 0 20 29 1 6 0 0 0 21 14 1 1 0 0 0 21 23 1 0 0 0 0 21 24 1 0 0 0 0 22 26 1 6 0 0 0 23 26 1 6 0 0 0 24 27 1 6 0 0 0 25 28 1 1 0 0 0 25 31 1 0 0 0 0 26 5 1 6 0 0 0 27 28 1 1 0 0 0 28 30 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	430.34
Volume:	473.796
LogP:	5.967
LogD:	5.423
LogS:	-5.537
# Rotatable Bonds:	5
TPSA:	49.69
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.547
Synthetic Accessibility Score:	5.646
Fsp3:	0.929
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.786
MDCK Permeability:	3.9228631067089736e-05
Pgp-inhibitor:	0.009
Pgp-substrate:	0.124
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.894
30% Bioavailability (F30%):	0.041

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.208
Plasma Protein Binding (PPB):	96.78852081298828%
Volume Distribution (VD):	1.181
Pgp-substrate:	2.1463935375213623%

ADMET: Metabolism

CYP1A2-inhibitor:	0.07
CYP1A2-substrate:	0.278
CYP2C19-inhibitor:	0.094
CYP2C19-substrate:	0.865
CYP2C9-inhibitor:	0.285
CYP2C9-substrate:	0.076
CYP2D6-inhibitor:	0.013
CYP2D6-substrate:	0.482
CYP3A4-inhibitor:	0.832
CYP3A4-substrate:	0.481

ADMET: Excretion

Clearance (CL):	7.641
Half-life (T1/2):	0.121

ADMET: Toxicity

hERG Blockers:	0.842
Human Hepatotoxicity (H-HT):	0.275
Drug-inuced Liver Injury (DILI):	0.835
AMES Toxicity:	0.025
Rat Oral Acute Toxicity:	0.02
Maximum Recommended Daily Dose:	0.202
Skin Sensitization:	0.954
Carcinogencity:	0.115
Eye Corrosion:	0.721
Eye Irritation:	0.512
Respiratory Toxicity:	0.609

Download Data

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

Natural Product: NPC473436

Natural Product ID:	NPC473436
*Common Name:**	DNWGDOYQDCNQQI-GUNASTJBSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	DNWGDOYQDCNQQI-GUNASTJBSA-N
Standard InCHI:	InChI=1S/C28H46O3/c1-17(2)18(3)6-7-19(4)22-8-9-23-21-14-25-28(30)15-20(29)10-13-27(28,16-31-25)24(21)11-12-26(22,23)5/h17,19-25,29-30H,3,6-16H2,1-2,4-5H3/t19-,20+,21+,22-,23+,24+,25-,26-,27+,28+/m1/s1
SMILES:	CC(C)C(=C)CCC(C)C1CCC2C1(CCC3C2CC4C5(C3(CCC(C5)O)CO4)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL430394
PubChem CID:	23642820
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0003567] Ergostane steroids

*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
NPO13916	Nephthea erecta	Species	Nephtheidae	Eukaryota	n.a.	formosan soft coral	n.a.	PMID[17845002]
NPO13916	Nephthea erecta	Species	Nephtheidae	Eukaryota	n.a.	Formosan soft coral	n.a.	PMID[24370010]
NPO13916	Nephthea erecta	Species	Nephtheidae	Eukaryota	n.a.	n.a.	n.a.	PMID[9722490]
NPO13916	Nephthea erecta	Species	Nephtheidae	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	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT139	Cell Line	HT-29	Homo sapiens	ED50	>	10.0	ug ml-1	PMID[486360]
NPT168	Cell Line	P388	Mus musculus	ED50	>	10.0	ug ml-1	PMID[486360]

☑ 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 NPC473436 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	223
0.1-0.2	2259
0.2-0.3	7428
0.3-0.4	14874
0.4-0.5	7273
0.5-0.6	4829
0.6-0.7	4203
0.7-0.8	1495
0.8-0.85	93
0.85-0.9	19
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9157	High Similarity	NPC85095
0.9157	High Similarity	NPC216420
0.9157	High Similarity	NPC211135
0.9048	High Similarity	NPC86238
0.8977	High Similarity	NPC219516
0.8837	High Similarity	NPC121981
0.878	High Similarity	NPC31828
0.8696	High Similarity	NPC316604
0.8675	High Similarity	NPC477282
0.8675	High Similarity	NPC81074
0.8605	High Similarity	NPC255882
0.8571	High Similarity	NPC475679
0.8571	High Similarity	NPC16449
0.8556	High Similarity	NPC210268
0.8537	High Similarity	NPC91573
0.8526	High Similarity	NPC68630
0.8526	High Similarity	NPC228049
0.8526	High Similarity	NPC52585
0.8523	High Similarity	NPC477600
0.8495	Intermediate Similarity	NPC476021
0.8495	Intermediate Similarity	NPC474994
0.8495	Intermediate Similarity	NPC476040
0.8488	Intermediate Similarity	NPC470929
0.8488	Intermediate Similarity	NPC232023
0.8462	Intermediate Similarity	NPC98193
0.8452	Intermediate Similarity	NPC475727
0.8452	Intermediate Similarity	NPC472742
0.8452	Intermediate Similarity	NPC80297
0.8452	Intermediate Similarity	NPC116119
0.8444	Intermediate Similarity	NPC10274
0.8434	Intermediate Similarity	NPC133596
0.8434	Intermediate Similarity	NPC64081
0.8434	Intermediate Similarity	NPC11907
0.8434	Intermediate Similarity	NPC474574
0.8415	Intermediate Similarity	NPC231680
0.8415	Intermediate Similarity	NPC270306
0.8415	Intermediate Similarity	NPC91387
0.8415	Intermediate Similarity	NPC3403
0.8409	Intermediate Similarity	NPC71520
0.8409	Intermediate Similarity	NPC269058
0.8404	Intermediate Similarity	NPC5358
0.8404	Intermediate Similarity	NPC216260
0.8391	Intermediate Similarity	NPC320824
0.8387	Intermediate Similarity	NPC169270
0.8387	Intermediate Similarity	NPC292718
0.8387	Intermediate Similarity	NPC306797
0.8387	Intermediate Similarity	NPC111834
0.8387	Intermediate Similarity	NPC472989
0.8333	Intermediate Similarity	NPC477817
0.8333	Intermediate Similarity	NPC109744
0.8333	Intermediate Similarity	NPC102708
0.8333	Intermediate Similarity	NPC477819
0.8298	Intermediate Similarity	NPC274793
0.8293	Intermediate Similarity	NPC228994
0.8293	Intermediate Similarity	NPC192501
0.8293	Intermediate Similarity	NPC308440
0.8293	Intermediate Similarity	NPC10476
0.8293	Intermediate Similarity	NPC472503
0.828	Intermediate Similarity	NPC241047
0.828	Intermediate Similarity	NPC8774
0.8276	Intermediate Similarity	NPC132635
0.8276	Intermediate Similarity	NPC207013
0.8247	Intermediate Similarity	NPC213190
0.8242	Intermediate Similarity	NPC473956
0.8242	Intermediate Similarity	NPC475751
0.8229	Intermediate Similarity	NPC49532
0.8214	Intermediate Similarity	NPC202540
0.8211	Intermediate Similarity	NPC102426
0.8211	Intermediate Similarity	NPC300179
0.8202	Intermediate Similarity	NPC155531
0.8202	Intermediate Similarity	NPC215968
0.8202	Intermediate Similarity	NPC125399
0.8202	Intermediate Similarity	NPC201273
0.82	Intermediate Similarity	NPC473570
0.8193	Intermediate Similarity	NPC196136
0.8193	Intermediate Similarity	NPC243027
0.8193	Intermediate Similarity	NPC158208
0.8191	Intermediate Similarity	NPC471903
0.8191	Intermediate Similarity	NPC210717
0.8191	Intermediate Similarity	NPC227583
0.8191	Intermediate Similarity	NPC98457
0.8191	Intermediate Similarity	NPC103165
0.8191	Intermediate Similarity	NPC12103
0.8182	Intermediate Similarity	NPC299963
0.8172	Intermediate Similarity	NPC144202
0.8172	Intermediate Similarity	NPC127718
0.8172	Intermediate Similarity	NPC65402
0.8163	Intermediate Similarity	NPC475521
0.8161	Intermediate Similarity	NPC475388
0.8161	Intermediate Similarity	NPC472504
0.8152	Intermediate Similarity	NPC114389
0.814	Intermediate Similarity	NPC13554
0.814	Intermediate Similarity	NPC78545
0.814	Intermediate Similarity	NPC71535
0.8132	Intermediate Similarity	NPC470361
0.8132	Intermediate Similarity	NPC74258
0.8125	Intermediate Similarity	NPC324598
0.8118	Intermediate Similarity	NPC301707
0.8118	Intermediate Similarity	NPC52755
0.8111	Intermediate Similarity	NPC186145
0.8111	Intermediate Similarity	NPC474657
0.8105	Intermediate Similarity	NPC253586
0.8105	Intermediate Similarity	NPC261807
0.8095	Intermediate Similarity	NPC93662
0.8095	Intermediate Similarity	NPC14112
0.8095	Intermediate Similarity	NPC470766
0.8095	Intermediate Similarity	NPC78067
0.8095	Intermediate Similarity	NPC278091
0.8095	Intermediate Similarity	NPC86305
0.8085	Intermediate Similarity	NPC30477
0.8081	Intermediate Similarity	NPC474015
0.8068	Intermediate Similarity	NPC477978
0.8068	Intermediate Similarity	NPC113978
0.8065	Intermediate Similarity	NPC137461
0.8065	Intermediate Similarity	NPC307776
0.8065	Intermediate Similarity	NPC27531
0.8065	Intermediate Similarity	NPC296620
0.8061	Intermediate Similarity	NPC475701
0.8049	Intermediate Similarity	NPC111234
0.8046	Intermediate Similarity	NPC70927
0.8043	Intermediate Similarity	NPC3345
0.8043	Intermediate Similarity	NPC329596
0.8043	Intermediate Similarity	NPC123252
0.8043	Intermediate Similarity	NPC291484
0.8043	Intermediate Similarity	NPC219937
0.8043	Intermediate Similarity	NPC80561
0.8043	Intermediate Similarity	NPC11216
0.8043	Intermediate Similarity	NPC194485
0.8043	Intermediate Similarity	NPC204188
0.8043	Intermediate Similarity	NPC53890
0.8041	Intermediate Similarity	NPC129372
0.8041	Intermediate Similarity	NPC289670
0.8041	Intermediate Similarity	NPC309425
0.8041	Intermediate Similarity	NPC88000
0.8041	Intermediate Similarity	NPC160734
0.8041	Intermediate Similarity	NPC4831
0.8041	Intermediate Similarity	NPC472023
0.8041	Intermediate Similarity	NPC47566
0.8041	Intermediate Similarity	NPC31346
0.8023	Intermediate Similarity	NPC80530
0.8023	Intermediate Similarity	NPC273410
0.8023	Intermediate Similarity	NPC24504
0.8023	Intermediate Similarity	NPC476316
0.8022	Intermediate Similarity	NPC133588
0.8022	Intermediate Similarity	NPC22376
0.8022	Intermediate Similarity	NPC128475
0.8022	Intermediate Similarity	NPC475664
0.8021	Intermediate Similarity	NPC280825
0.8021	Intermediate Similarity	NPC476895
0.8021	Intermediate Similarity	NPC234287
0.8	Intermediate Similarity	NPC6605
0.8	Intermediate Similarity	NPC477283
0.8	Intermediate Similarity	NPC128951
0.8	Intermediate Similarity	NPC192046
0.8	Intermediate Similarity	NPC302578
0.8	Intermediate Similarity	NPC288970
0.8	Intermediate Similarity	NPC477227
0.8	Intermediate Similarity	NPC94462
0.8	Intermediate Similarity	NPC105208
0.798	Intermediate Similarity	NPC85593
0.798	Intermediate Similarity	NPC31430
0.798	Intermediate Similarity	NPC165033
0.798	Intermediate Similarity	NPC474464
0.798	Intermediate Similarity	NPC273879
0.7978	Intermediate Similarity	NPC256567
0.7976	Intermediate Similarity	NPC104387
0.7976	Intermediate Similarity	NPC212879
0.7976	Intermediate Similarity	NPC178383
0.7976	Intermediate Similarity	NPC70982
0.7976	Intermediate Similarity	NPC103822
0.7976	Intermediate Similarity	NPC230704
0.7976	Intermediate Similarity	NPC240235
0.7976	Intermediate Similarity	NPC185536
0.7976	Intermediate Similarity	NPC231256
0.7959	Intermediate Similarity	NPC136816
0.7957	Intermediate Similarity	NPC275671
0.7957	Intermediate Similarity	NPC130840
0.7957	Intermediate Similarity	NPC97404
0.7957	Intermediate Similarity	NPC48463
0.7957	Intermediate Similarity	NPC41554
0.7955	Intermediate Similarity	NPC202688
0.7955	Intermediate Similarity	NPC60018
0.7955	Intermediate Similarity	NPC30166
0.7955	Intermediate Similarity	NPC477599
0.7955	Intermediate Similarity	NPC154043
0.7952	Intermediate Similarity	NPC95165
0.7938	Intermediate Similarity	NPC108371
0.7938	Intermediate Similarity	NPC471247
0.7938	Intermediate Similarity	NPC473200
0.7938	Intermediate Similarity	NPC7341
0.7938	Intermediate Similarity	NPC317019
0.7935	Intermediate Similarity	NPC105495
0.7931	Intermediate Similarity	NPC236112
0.7931	Intermediate Similarity	NPC206735
0.7931	Intermediate Similarity	NPC322313
0.7931	Intermediate Similarity	NPC102253
0.7931	Intermediate Similarity	NPC236237
0.7931	Intermediate Similarity	NPC47149
0.7927	Intermediate Similarity	NPC45296
0.7921	Intermediate Similarity	NPC473517

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 NPC473436 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	224
0.1-0.2	2639
0.2-0.3	4163
0.3-0.4	1416
0.4-0.5	344
0.5-0.6	180
0.6-0.7	173
0.7-0.8	11
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
0.7931	Intermediate Similarity	NPD7525	Registered
0.7717	Intermediate Similarity	NPD7524	Approved
0.759	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7364	Intermediate Similarity	NPD7516	Approved
0.7333	Intermediate Similarity	NPD6928	Phase 2
0.7283	Intermediate Similarity	NPD6695	Phase 3
0.7273	Intermediate Similarity	NPD7327	Approved
0.7273	Intermediate Similarity	NPD7328	Approved
0.7222	Intermediate Similarity	NPD7645	Phase 2
0.7159	Intermediate Similarity	NPD7339	Approved
0.7159	Intermediate Similarity	NPD6942	Approved
0.7143	Intermediate Similarity	NPD6931	Approved
0.7143	Intermediate Similarity	NPD8171	Discontinued
0.7143	Intermediate Similarity	NPD6930	Phase 2
0.7128	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD8296	Approved
0.708	Intermediate Similarity	NPD8380	Approved
0.708	Intermediate Similarity	NPD8378	Approved
0.708	Intermediate Similarity	NPD8335	Approved
0.708	Intermediate Similarity	NPD8379	Approved
0.7079	Intermediate Similarity	NPD6933	Approved
0.7041	Intermediate Similarity	NPD8034	Phase 2
0.7041	Intermediate Similarity	NPD8035	Phase 2
0.7033	Intermediate Similarity	NPD6929	Approved
0.7	Intermediate Similarity	NPD6932	Approved
0.6991	Remote Similarity	NPD8377	Approved
0.6991	Remote Similarity	NPD8294	Approved
0.6988	Remote Similarity	NPD371	Approved
0.6979	Remote Similarity	NPD7750	Discontinued
0.6961	Remote Similarity	NPD7638	Approved
0.693	Remote Similarity	NPD8033	Approved
0.6909	Remote Similarity	NPD8133	Approved
0.6893	Remote Similarity	NPD7639	Approved
0.6893	Remote Similarity	NPD7640	Approved
0.6889	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD6924	Approved
0.6854	Remote Similarity	NPD6926	Approved
0.6848	Remote Similarity	NPD6683	Phase 2
0.6842	Remote Similarity	NPD6059	Approved
0.6842	Remote Similarity	NPD6054	Approved
0.6827	Remote Similarity	NPD4159	Approved
0.6813	Remote Similarity	NPD6925	Approved
0.6813	Remote Similarity	NPD5776	Phase 2
0.6804	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD7514	Phase 3
0.6771	Remote Similarity	NPD6893	Approved
0.6759	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD7145	Approved
0.6737	Remote Similarity	NPD4788	Approved
0.6724	Remote Similarity	NPD6370	Approved
0.6705	Remote Similarity	NPD4787	Phase 1
0.67	Remote Similarity	NPD7087	Discontinued
0.6697	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD7507	Approved
0.6667	Remote Similarity	NPD6412	Phase 2
0.6667	Remote Similarity	NPD4786	Approved
0.6667	Remote Similarity	NPD7319	Approved
0.6667	Remote Similarity	NPD5328	Approved
0.6638	Remote Similarity	NPD6015	Approved
0.6638	Remote Similarity	NPD6016	Approved
0.6634	Remote Similarity	NPD4202	Approved
0.6629	Remote Similarity	NPD4243	Approved
0.661	Remote Similarity	NPD7492	Approved
0.6607	Remote Similarity	NPD4632	Approved
0.6606	Remote Similarity	NPD7320	Approved
0.6596	Remote Similarity	NPD4748	Discontinued
0.6596	Remote Similarity	NPD7332	Phase 2
0.6596	Remote Similarity	NPD7509	Discontinued
0.6583	Remote Similarity	NPD7736	Approved
0.6581	Remote Similarity	NPD5988	Approved
0.6574	Remote Similarity	NPD7128	Approved
0.6574	Remote Similarity	NPD6675	Approved
0.6574	Remote Similarity	NPD6402	Approved
0.6574	Remote Similarity	NPD5739	Approved
0.6559	Remote Similarity	NPD6697	Approved
0.6559	Remote Similarity	NPD6115	Approved
0.6559	Remote Similarity	NPD6118	Approved
0.6559	Remote Similarity	NPD6114	Approved
0.6555	Remote Similarity	NPD6616	Approved
0.6552	Remote Similarity	NPD6319	Approved
0.6538	Remote Similarity	NPD4755	Approved
0.6535	Remote Similarity	NPD6079	Approved
0.6531	Remote Similarity	NPD3618	Phase 1
0.6526	Remote Similarity	NPD6898	Phase 1
0.6526	Remote Similarity	NPD6902	Approved
0.6518	Remote Similarity	NPD8297	Approved
0.65	Remote Similarity	NPD8293	Discontinued
0.65	Remote Similarity	NPD7078	Approved
0.6496	Remote Similarity	NPD7503	Approved
0.6486	Remote Similarity	NPD4634	Approved
0.6484	Remote Similarity	NPD4785	Approved
0.6484	Remote Similarity	NPD4784	Approved
0.6481	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD6399	Phase 3
0.6458	Remote Similarity	NPD3667	Approved
0.6455	Remote Similarity	NPD6881	Approved
0.6455	Remote Similarity	NPD6899	Approved
0.6452	Remote Similarity	NPD6116	Phase 1
0.6449	Remote Similarity	NPD7632	Discontinued
0.6444	Remote Similarity	NPD7152	Approved
0.6444	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD7150	Approved
0.6444	Remote Similarity	NPD7151	Approved
0.6422	Remote Similarity	NPD6008	Approved
0.6415	Remote Similarity	NPD5285	Approved
0.6415	Remote Similarity	NPD4696	Approved
0.6415	Remote Similarity	NPD4700	Approved
0.6415	Remote Similarity	NPD5286	Approved
0.6413	Remote Similarity	NPD3703	Phase 2
0.6404	Remote Similarity	NPD6922	Approved
0.6404	Remote Similarity	NPD6923	Approved
0.6396	Remote Similarity	NPD6373	Approved
0.6396	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6396	Remote Similarity	NPD6372	Approved
0.6364	Remote Similarity	NPD5697	Approved
0.6364	Remote Similarity	NPD5701	Approved
0.6355	Remote Similarity	NPD5344	Discontinued
0.6344	Remote Similarity	NPD6117	Approved
0.6339	Remote Similarity	NPD7290	Approved
0.6339	Remote Similarity	NPD6883	Approved
0.6339	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6339	Remote Similarity	NPD7102	Approved
0.6333	Remote Similarity	NPD7144	Approved
0.6333	Remote Similarity	NPD7143	Approved
0.6321	Remote Similarity	NPD4225	Approved
0.6311	Remote Similarity	NPD6033	Approved
0.6304	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD5224	Approved
0.6296	Remote Similarity	NPD5211	Phase 2
0.6296	Remote Similarity	NPD5226	Approved
0.6296	Remote Similarity	NPD5225	Approved
0.6296	Remote Similarity	NPD4633	Approved
0.6293	Remote Similarity	NPD7115	Discovery
0.6293	Remote Similarity	NPD6009	Approved
0.6283	Remote Similarity	NPD6649	Approved
0.6283	Remote Similarity	NPD6847	Approved
0.6283	Remote Similarity	NPD6869	Approved
0.6283	Remote Similarity	NPD6650	Approved
0.6283	Remote Similarity	NPD6617	Approved
0.6283	Remote Similarity	NPD8130	Phase 1
0.6275	Remote Similarity	NPD3168	Discontinued
0.625	Remote Similarity	NPD6067	Discontinued
0.625	Remote Similarity	NPD6014	Approved
0.625	Remote Similarity	NPD6012	Approved
0.625	Remote Similarity	NPD6013	Approved
0.625	Remote Similarity	NPD7604	Phase 2
0.6239	Remote Similarity	NPD5175	Approved
0.6239	Remote Similarity	NPD5174	Approved
0.6237	Remote Similarity	NPD4190	Phase 3
0.6237	Remote Similarity	NPD5275	Approved
0.6228	Remote Similarity	NPD6882	Approved
0.6226	Remote Similarity	NPD6083	Phase 2
0.6226	Remote Similarity	NPD6084	Phase 2
0.6222	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6218	Remote Similarity	NPD5983	Phase 2
0.6214	Remote Similarity	NPD7637	Suspended
0.6204	Remote Similarity	NPD5223	Approved
0.619	Remote Similarity	NPD7991	Discontinued
0.6182	Remote Similarity	NPD5141	Approved
0.6176	Remote Similarity	NPD4753	Phase 2
0.6162	Remote Similarity	NPD3665	Phase 1
0.6162	Remote Similarity	NPD3133	Approved
0.6162	Remote Similarity	NPD3666	Approved
0.6161	Remote Similarity	NPD6686	Approved
0.6161	Remote Similarity	NPD6011	Approved
0.6154	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6148	Remote Similarity	NPD6336	Discontinued
0.6146	Remote Similarity	NPD4195	Approved
0.614	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6132	Remote Similarity	NPD5222	Approved
0.6132	Remote Similarity	NPD4697	Phase 3
0.6132	Remote Similarity	NPD5221	Approved
0.6132	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6126	Remote Similarity	NPD4768	Approved
0.6126	Remote Similarity	NPD4767	Approved
0.6111	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD5360	Phase 3
0.6095	Remote Similarity	NPD7748	Approved
0.6091	Remote Similarity	NPD4754	Approved
0.6083	Remote Similarity	NPD6921	Approved
0.6075	Remote Similarity	NPD7902	Approved
0.6075	Remote Similarity	NPD5173	Approved
0.6071	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6058	Remote Similarity	NPD7515	Phase 2
0.6055	Remote Similarity	NPD1700	Approved
0.6047	Remote Similarity	NPD1145	Discontinued
0.6042	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6038	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD6051	Approved
0.6018	Remote Similarity	NPD5128	Approved
0.6018	Remote Similarity	NPD4729	Approved
0.6018	Remote Similarity	NPD4730	Approved
0.6017	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.5984	Remote Similarity	NPD8449	Approved
0.5984	Remote Similarity	NPD8328	Phase 3
0.5982	Remote Similarity	NPD6640	Phase 3
0.5978	Remote Similarity	NPD4245	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