NPASS Compound

Structure

NPC4620 OpenBabel07101718302D 42 44 0 0 1 0 0 0 0 0999 V2000 -2.4346 -2.3731 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7385 -0.6043 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1345 -4.6485 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8748 -2.6576 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7092 2.2754 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8504 -1.3443 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8625 0.2425 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3977 1.8710 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1982 -2.0710 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3514 -2.5599 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5046 -1.0932 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5046 -2.0710 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8918 -1.0932 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1069 -4.5463 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4771 -3.5508 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6817 2.1732 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1982 -1.0932 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9299 -0.3021 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -3.1642 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9299 -2.8620 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5046 -1.0932 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9299 -2.8620 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9299 -0.3021 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9299 1.2799 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5046 -2.0710 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.3514 -0.6043 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 0.9778 0.0000 C 0 0 1 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 4.8918 -2.0710 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6817 -5.3373 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0518 -4.3419 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2564 2.9642 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -4.1419 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2321 2.2098 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8403 0.2425 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9724 1.0800 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.9778 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0450 -0.6043 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5046 -3.6530 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5046 -3.6530 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0794 1.2799 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5046 0.4889 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 12 1 0 0 0 0 2 13 1 0 0 0 0 3 14 1 0 0 0 0 4 15 1 0 0 0 0 5 16 1 0 0 0 0 8 27 1 0 0 0 0 9 10 2 0 0 0 0 9 17 1 0 0 0 0 10 25 1 0 0 0 0 11 12 2 0 0 0 0 11 18 1 0 0 0 0 12 20 1 0 0 0 0 13 29 2 0 0 0 0 13 38 1 0 0 0 0 14 30 2 0 0 0 0 14 39 1 0 0 0 0 15 31 2 0 0 0 0 15 40 1 0 0 0 0 16 32 2 0 0 0 0 16 41 1 0 0 0 0 17 26 1 6 0 0 0 17 38 1 0 0 0 0 18 28 1 6 0 0 0 18 42 1 0 0 0 0 19 20 1 0 0 0 0 19 22 1 0 0 0 0 19 33 1 6 0 0 0 20 39 1 1 0 0 0 21 23 1 0 0 0 0 21 25 1 1 0 0 0 21 26 1 0 0 0 0 22 25 1 6 0 0 0 22 40 1 0 0 0 0 23 28 1 1 0 0 0 23 41 1 0 0 0 0 24 27 1 0 0 0 0 24 34 2 0 0 0 0 24 42 1 0 0 0 0 25 6 1 1 0 0 0 26 7 1 1 0 0 0 26 35 1 0 0 0 0 27 28 1 6 0 0 0 27 36 1 0 0 0 0 28 37 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	598.23
Volume:	571.783
LogP:	1.169
LogD:	0.255
LogS:	-3.447
# Rotatable Bonds:	8
TPSA:	212.42
# H-Bond Aceptor:	14
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	14

MedChem Properties

QED Drug-Likeness Score:	0.181
Synthetic Accessibility Score:	5.958
Fsp3:	0.679
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
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:	-5.489
MDCK Permeability:	0.00026443181559443474
Pgp-inhibitor:	0.995
Pgp-substrate:	0.988
Human Intestinal Absorption (HIA):	0.844
20% Bioavailability (F20%):	0.646
30% Bioavailability (F30%):	0.992

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.152
Plasma Protein Binding (PPB):	28.32245445251465%
Volume Distribution (VD):	0.959
Pgp-substrate:	44.2188720703125%

ADMET: Metabolism

CYP1A2-inhibitor:	0.008
CYP1A2-substrate:	0.045
CYP2C19-inhibitor:	0.007
CYP2C19-substrate:	0.062
CYP2C9-inhibitor:	0.0
CYP2C9-substrate:	0.011
CYP2D6-inhibitor:	0.024
CYP2D6-substrate:	0.038
CYP3A4-inhibitor:	0.48
CYP3A4-substrate:	0.197

ADMET: Excretion

Clearance (CL):	1.966
Half-life (T1/2):	0.116

ADMET: Toxicity

hERG Blockers:	0.029
Human Hepatotoxicity (H-HT):	0.862
Drug-inuced Liver Injury (DILI):	0.836
AMES Toxicity:	0.105
Rat Oral Acute Toxicity:	0.694
Maximum Recommended Daily Dose:	0.004
Skin Sensitization:	0.409
Carcinogencity:	0.141
Eye Corrosion:	0.004
Eye Irritation:	0.013
Respiratory Toxicity:	0.982

Download Data

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

Natural Product: NPC4620

Natural Product ID:	NPC4620
*Common Name:**	Brianodin B
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	WRMRTVQZNMWLDP-ARBHOCKGSA-N
Standard InCHI:	InChI=1S/C28H38O14/c1-12-11-18-28(37,27(8,36)24(34)42-18)23(41-16(5)32)21-25(6,10-9-17(26(21,7)35)38-13(2)29)22(40-15(4)31)19(33)20(12)39-14(3)30/h9-11,17-23,33,35-37H,1-8H3/b12-11-/t17-,18+,19-,20+,21-,22-,23+,25+,26-,27-,28+/m1/s1
SMILES:	C/C/1=C/[C@H]2[C@]([C@H]([C@@H]3[C@](C)(C=C[C@H]([C@@]3(C)O)OC(=O)C)[C@@H]([C@@H]([C@H]1OC(=O)C)O)OC(=O)C)OC(=O)C)([C@@](C)(C(=O)O2)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL503794
PubChem CID:	24862327
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001538] Diterpene lactones

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO33024	pachyclavularia sp.	Species	Clavulariidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18345642]

☑ 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
IC50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[486043]

☑ 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 NPC4620 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	212
0.1-0.2	1154
0.2-0.3	4247
0.3-0.4	8047
0.4-0.5	14103
0.5-0.6	7375
0.6-0.7	5813
0.7-0.8	1603
0.8-0.85	102
0.85-0.9	17
0.9-0.95	18
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9896	High Similarity	NPC220964
0.9896	High Similarity	NPC475676
0.9694	High Similarity	NPC326994
0.9694	High Similarity	NPC324327
0.9694	High Similarity	NPC194620
0.9694	High Similarity	NPC72813
0.9694	High Similarity	NPC474421
0.9596	High Similarity	NPC14862
0.9596	High Similarity	NPC55972
0.9596	High Similarity	NPC233379
0.9596	High Similarity	NPC474664
0.9596	High Similarity	NPC169888
0.9596	High Similarity	NPC327286
0.9592	High Similarity	NPC16313
0.9592	High Similarity	NPC9303
0.95	High Similarity	NPC15218
0.9394	High Similarity	NPC475802
0.9388	High Similarity	NPC69171
0.9388	High Similarity	NPC474165
0.9307	High Similarity	NPC475922
0.9286	High Similarity	NPC183571
0.9216	High Similarity	NPC161816
0.9216	High Similarity	NPC115257
0.9118	High Similarity	NPC42662
0.8857	High Similarity	NPC473877
0.8812	High Similarity	NPC474166
0.8812	High Similarity	NPC19239
0.8725	High Similarity	NPC472756
0.8713	High Similarity	NPC472754
0.8713	High Similarity	NPC149371
0.8654	High Similarity	NPC94377
0.8614	High Similarity	NPC47880
0.8614	High Similarity	NPC472753
0.8611	High Similarity	NPC474333
0.86	High Similarity	NPC471144
0.8532	High Similarity	NPC296822
0.8529	High Similarity	NPC471148
0.8447	Intermediate Similarity	NPC475871
0.8447	Intermediate Similarity	NPC472755
0.8447	Intermediate Similarity	NPC475945
0.8431	Intermediate Similarity	NPC164598
0.8431	Intermediate Similarity	NPC474339
0.8421	Intermediate Similarity	NPC478112
0.8381	Intermediate Similarity	NPC475587
0.8381	Intermediate Similarity	NPC475510
0.8381	Intermediate Similarity	NPC477513
0.8365	Intermediate Similarity	NPC258532
0.8365	Intermediate Similarity	NPC472748
0.835	Intermediate Similarity	NPC474747
0.8349	Intermediate Similarity	NPC73314
0.8333	Intermediate Similarity	NPC317687
0.8333	Intermediate Similarity	NPC475949
0.8318	Intermediate Similarity	NPC281624
0.8318	Intermediate Similarity	NPC5103
0.8302	Intermediate Similarity	NPC473595
0.8302	Intermediate Similarity	NPC473939
0.83	Intermediate Similarity	NPC36954
0.8286	Intermediate Similarity	NPC472749
0.8286	Intermediate Similarity	NPC472751
0.8283	Intermediate Similarity	NPC476300
0.8269	Intermediate Similarity	NPC472747
0.8269	Intermediate Similarity	NPC472750
0.8257	Intermediate Similarity	NPC469496
0.8257	Intermediate Similarity	NPC469463
0.8257	Intermediate Similarity	NPC469454
0.8252	Intermediate Similarity	NPC474742
0.8241	Intermediate Similarity	NPC317107
0.8218	Intermediate Similarity	NPC76862
0.8218	Intermediate Similarity	NPC54731
0.8218	Intermediate Similarity	NPC158416
0.8218	Intermediate Similarity	NPC470883
0.8218	Intermediate Similarity	NPC473859
0.8218	Intermediate Similarity	NPC230800
0.8218	Intermediate Similarity	NPC279621
0.8218	Intermediate Similarity	NPC39859
0.8208	Intermediate Similarity	NPC26617
0.8198	Intermediate Similarity	NPC476712
0.8198	Intermediate Similarity	NPC476713
0.819	Intermediate Similarity	NPC146731
0.819	Intermediate Similarity	NPC296950
0.819	Intermediate Similarity	NPC203659
0.819	Intermediate Similarity	NPC474741
0.8182	Intermediate Similarity	NPC30515
0.8182	Intermediate Similarity	NPC184463
0.8173	Intermediate Similarity	NPC474709
0.8155	Intermediate Similarity	NPC288876
0.8148	Intermediate Similarity	NPC473975
0.8148	Intermediate Similarity	NPC473843
0.8148	Intermediate Similarity	NPC473594
0.8148	Intermediate Similarity	NPC474586
0.8137	Intermediate Similarity	NPC40812
0.8137	Intermediate Similarity	NPC471140
0.8119	Intermediate Similarity	NPC471142
0.8119	Intermediate Similarity	NPC475659
0.8108	Intermediate Similarity	NPC476711
0.8108	Intermediate Similarity	NPC476710
0.81	Intermediate Similarity	NPC475912
0.8095	Intermediate Similarity	NPC475321
0.8095	Intermediate Similarity	NPC110989
0.8081	Intermediate Similarity	NPC474232
0.8081	Intermediate Similarity	NPC475855
0.8081	Intermediate Similarity	NPC51004
0.8073	Intermediate Similarity	NPC304180
0.8073	Intermediate Similarity	NPC179798
0.8073	Intermediate Similarity	NPC194619
0.8061	Intermediate Similarity	NPC476803
0.8058	Intermediate Similarity	NPC222303
0.8053	Intermediate Similarity	NPC470186
0.8041	Intermediate Similarity	NPC278283
0.8039	Intermediate Similarity	NPC476315
0.8039	Intermediate Similarity	NPC476009
0.8036	Intermediate Similarity	NPC473590
0.802	Intermediate Similarity	NPC474247
0.8	Intermediate Similarity	NPC105725
0.8	Intermediate Similarity	NPC225353
0.8	Intermediate Similarity	NPC475972
0.8	Intermediate Similarity	NPC320019
0.8	Intermediate Similarity	NPC66108
0.8	Intermediate Similarity	NPC473596
0.8	Intermediate Similarity	NPC324017
0.7982	Intermediate Similarity	NPC475134
0.7982	Intermediate Similarity	NPC235014
0.7982	Intermediate Similarity	NPC475563
0.798	Intermediate Similarity	NPC473564
0.798	Intermediate Similarity	NPC307411
0.7963	Intermediate Similarity	NPC476479
0.7963	Intermediate Similarity	NPC151393
0.7963	Intermediate Similarity	NPC308191
0.7963	Intermediate Similarity	NPC322903
0.7961	Intermediate Similarity	NPC134454
0.7961	Intermediate Similarity	NPC17326
0.7944	Intermediate Similarity	NPC179891
0.7944	Intermediate Similarity	NPC123726
0.7944	Intermediate Similarity	NPC477125
0.7944	Intermediate Similarity	NPC284365
0.7941	Intermediate Similarity	NPC14961
0.7941	Intermediate Similarity	NPC107476
0.7941	Intermediate Similarity	NPC475900
0.7941	Intermediate Similarity	NPC270013
0.7941	Intermediate Similarity	NPC471141
0.7931	Intermediate Similarity	NPC67251
0.7928	Intermediate Similarity	NPC477126
0.7928	Intermediate Similarity	NPC56448
0.7925	Intermediate Similarity	NPC474775
0.7925	Intermediate Similarity	NPC475873
0.7921	Intermediate Similarity	NPC212486
0.7921	Intermediate Similarity	NPC475838
0.7921	Intermediate Similarity	NPC469645
0.7921	Intermediate Similarity	NPC81419
0.7921	Intermediate Similarity	NPC475302
0.7921	Intermediate Similarity	NPC125674
0.7921	Intermediate Similarity	NPC469692
0.7921	Intermediate Similarity	NPC179746
0.7921	Intermediate Similarity	NPC228451
0.7909	Intermediate Similarity	NPC473921
0.7909	Intermediate Similarity	NPC126897
0.7909	Intermediate Similarity	NPC475480
0.7909	Intermediate Similarity	NPC475668
0.7909	Intermediate Similarity	NPC287311
0.7909	Intermediate Similarity	NPC297945
0.7905	Intermediate Similarity	NPC15993
0.7905	Intermediate Similarity	NPC264477
0.7905	Intermediate Similarity	NPC477511
0.7905	Intermediate Similarity	NPC201718
0.79	Intermediate Similarity	NPC469368
0.79	Intermediate Similarity	NPC179394
0.79	Intermediate Similarity	NPC473619
0.79	Intermediate Similarity	NPC476004
0.79	Intermediate Similarity	NPC474761
0.79	Intermediate Similarity	NPC473448
0.79	Intermediate Similarity	NPC144133
0.79	Intermediate Similarity	NPC316228
0.789	Intermediate Similarity	NPC477102
0.7885	Intermediate Similarity	NPC161855
0.7885	Intermediate Similarity	NPC187761
0.7885	Intermediate Similarity	NPC473326
0.7885	Intermediate Similarity	NPC83895
0.7885	Intermediate Similarity	NPC308567
0.7885	Intermediate Similarity	NPC261377
0.7885	Intermediate Similarity	NPC255592
0.7879	Intermediate Similarity	NPC202672
0.7879	Intermediate Similarity	NPC476805
0.7876	Intermediate Similarity	NPC471145
0.7876	Intermediate Similarity	NPC23046
0.7876	Intermediate Similarity	NPC176513
0.7876	Intermediate Similarity	NPC471146
0.7876	Intermediate Similarity	NPC470775
0.787	Intermediate Similarity	NPC112780
0.7864	Intermediate Similarity	NPC21302
0.7864	Intermediate Similarity	NPC469528
0.7864	Intermediate Similarity	NPC17585
0.7864	Intermediate Similarity	NPC306041
0.7864	Intermediate Similarity	NPC477921
0.7864	Intermediate Similarity	NPC469369
0.7864	Intermediate Similarity	NPC11396
0.7857	Intermediate Similarity	NPC469910
0.785	Intermediate Similarity	NPC471143
0.785	Intermediate Similarity	NPC477510
0.7845	Intermediate Similarity	NPC310035
0.7845	Intermediate Similarity	NPC188222

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 NPC4620 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	178
0.1-0.2	1679
0.2-0.3	3622
0.3-0.4	2349
0.4-0.5	800
0.5-0.6	356
0.6-0.7	147
0.7-0.8	18
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8208	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7909	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.79	Intermediate Similarity	NPD46	Approved
0.79	Intermediate Similarity	NPD6698	Approved
0.7822	Intermediate Similarity	NPD7983	Approved
0.7818	Intermediate Similarity	NPD6371	Approved
0.767	Intermediate Similarity	NPD5282	Discontinued
0.7477	Intermediate Similarity	NPD6686	Approved
0.7458	Intermediate Similarity	NPD8513	Phase 3
0.7458	Intermediate Similarity	NPD8517	Approved
0.7458	Intermediate Similarity	NPD8516	Approved
0.7458	Intermediate Similarity	NPD8515	Approved
0.7429	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7404	Intermediate Similarity	NPD5779	Approved
0.7404	Intermediate Similarity	NPD5778	Approved
0.7383	Intermediate Similarity	NPD4225	Approved
0.7379	Intermediate Similarity	NPD7838	Discovery
0.7321	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7265	Intermediate Similarity	NPD7115	Discovery
0.7228	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD5785	Approved
0.7154	Intermediate Similarity	NPD8074	Phase 3
0.7143	Intermediate Similarity	NPD6411	Approved
0.7083	Intermediate Similarity	NPD6319	Approved
0.7064	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5369	Approved
0.6981	Remote Similarity	NPD7637	Suspended
0.6957	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD6101	Approved
0.6937	Remote Similarity	NPD5344	Discontinued
0.6931	Remote Similarity	NPD4270	Approved
0.6931	Remote Similarity	NPD4269	Approved
0.6923	Remote Similarity	NPD4251	Approved
0.6923	Remote Similarity	NPD4250	Approved
0.6897	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD7839	Suspended
0.6863	Remote Similarity	NPD7154	Phase 3
0.6855	Remote Similarity	NPD7492	Approved
0.6833	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6827	Remote Similarity	NPD5786	Approved
0.6827	Remote Similarity	NPD4249	Approved
0.6803	Remote Similarity	NPD6054	Approved
0.68	Remote Similarity	NPD6616	Approved
0.6794	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD1695	Approved
0.678	Remote Similarity	NPD8297	Approved
0.678	Remote Similarity	NPD6053	Discontinued
0.6774	Remote Similarity	NPD8328	Phase 3
0.6772	Remote Similarity	NPD7319	Approved
0.6759	Remote Similarity	NPD6399	Phase 3
0.6757	Remote Similarity	NPD7638	Approved
0.6748	Remote Similarity	NPD6921	Approved
0.6746	Remote Similarity	NPD7078	Approved
0.6733	Remote Similarity	NPD4822	Approved
0.6733	Remote Similarity	NPD4821	Approved
0.6733	Remote Similarity	NPD4252	Approved
0.6733	Remote Similarity	NPD4819	Approved
0.6733	Remote Similarity	NPD4820	Approved
0.6733	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD1694	Approved
0.6731	Remote Similarity	NPD5363	Approved
0.6723	Remote Similarity	NPD4632	Approved
0.67	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD5362	Discontinued
0.6696	Remote Similarity	NPD7640	Approved
0.6696	Remote Similarity	NPD7639	Approved
0.6695	Remote Similarity	NPD6649	Approved
0.6695	Remote Similarity	NPD6650	Approved
0.6694	Remote Similarity	NPD6370	Approved
0.6693	Remote Similarity	NPD7736	Approved
0.6667	Remote Similarity	NPD6372	Approved
0.6667	Remote Similarity	NPD6059	Approved
0.6667	Remote Similarity	NPD6083	Phase 2
0.6667	Remote Similarity	NPD7507	Approved
0.6667	Remote Similarity	NPD6084	Phase 2
0.6667	Remote Similarity	NPD7260	Phase 2
0.6667	Remote Similarity	NPD6373	Approved
0.6667	Remote Similarity	NPD8273	Phase 1
0.6667	Remote Similarity	NPD8451	Approved
0.6638	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6638	Remote Similarity	NPD6412	Phase 2
0.6614	Remote Similarity	NPD8293	Discontinued
0.6614	Remote Similarity	NPD8448	Approved
0.6613	Remote Similarity	NPD6015	Approved
0.6613	Remote Similarity	NPD6016	Approved
0.6602	Remote Similarity	NPD6435	Approved
0.6583	Remote Similarity	NPD8133	Approved
0.6581	Remote Similarity	NPD6881	Approved
0.6581	Remote Similarity	NPD6899	Approved
0.6571	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD8039	Approved
0.656	Remote Similarity	NPD5988	Approved
0.6552	Remote Similarity	NPD6402	Approved
0.6552	Remote Similarity	NPD5739	Approved
0.6552	Remote Similarity	NPD6675	Approved
0.6552	Remote Similarity	NPD7128	Approved
0.6549	Remote Similarity	NPD6648	Approved
0.6538	Remote Similarity	NPD6110	Phase 1
0.6535	Remote Similarity	NPD4271	Approved
0.6535	Remote Similarity	NPD4268	Approved
0.6525	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6508	Remote Similarity	NPD7642	Approved
0.65	Remote Similarity	NPD6882	Approved
0.6496	Remote Similarity	NPD5697	Approved
0.6486	Remote Similarity	NPD5695	Phase 3
0.648	Remote Similarity	NPD7503	Approved
0.648	Remote Similarity	NPD8444	Approved
0.6471	Remote Similarity	NPD4634	Approved
0.6471	Remote Similarity	NPD7290	Approved
0.6471	Remote Similarity	NPD7102	Approved
0.6471	Remote Similarity	NPD6883	Approved
0.6462	Remote Similarity	NPD8391	Approved
0.6462	Remote Similarity	NPD8390	Approved
0.6462	Remote Similarity	NPD8392	Approved
0.646	Remote Similarity	NPD5696	Approved
0.6457	Remote Similarity	NPD8341	Approved
0.6457	Remote Similarity	NPD8299	Approved
0.6457	Remote Similarity	NPD8340	Approved
0.6457	Remote Similarity	NPD8342	Approved
0.6449	Remote Similarity	NPD7524	Approved
0.6442	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6441	Remote Similarity	NPD7320	Approved
0.6423	Remote Similarity	NPD6009	Approved
0.6417	Remote Similarity	NPD6617	Approved
0.6417	Remote Similarity	NPD6869	Approved
0.6417	Remote Similarity	NPD6847	Approved
0.6417	Remote Similarity	NPD2204	Approved
0.6417	Remote Similarity	NPD8130	Phase 1
0.6408	Remote Similarity	NPD5368	Approved
0.6387	Remote Similarity	NPD6014	Approved
0.6387	Remote Similarity	NPD6012	Approved
0.6387	Remote Similarity	NPD6013	Approved
0.6378	Remote Similarity	NPD7830	Approved
0.6378	Remote Similarity	NPD7604	Phase 2
0.6378	Remote Similarity	NPD7829	Approved
0.6371	Remote Similarity	NPD7328	Approved
0.6371	Remote Similarity	NPD7327	Approved
0.6364	Remote Similarity	NPD6845	Suspended
0.6356	Remote Similarity	NPD5701	Approved
0.6349	Remote Similarity	NPD8033	Approved
0.6349	Remote Similarity	NPD5983	Phase 2
0.6333	Remote Similarity	NPD6421	Discontinued
0.6321	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.632	Remote Similarity	NPD7516	Approved
0.6303	Remote Similarity	NPD6011	Approved
0.6286	Remote Similarity	NPD5209	Approved
0.6283	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6279	Remote Similarity	NPD6336	Discontinued
0.6271	Remote Similarity	NPD6008	Approved
0.627	Remote Similarity	NPD8294	Approved
0.627	Remote Similarity	NPD8377	Approved
0.6239	Remote Similarity	NPD5737	Approved
0.6239	Remote Similarity	NPD6672	Approved
0.6228	Remote Similarity	NPD7902	Approved
0.6226	Remote Similarity	NPD6695	Phase 3
0.6226	Remote Similarity	NPD5332	Approved
0.6226	Remote Similarity	NPD5331	Approved
0.622	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.622	Remote Similarity	NPD8380	Approved
0.622	Remote Similarity	NPD8378	Approved
0.622	Remote Similarity	NPD8296	Approved
0.622	Remote Similarity	NPD8335	Approved
0.622	Remote Similarity	NPD8379	Approved
0.6216	Remote Similarity	NPD5693	Phase 1
0.6216	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6212	Remote Similarity	NPD5956	Approved
0.6211	Remote Similarity	NPD3197	Phase 1
0.6195	Remote Similarity	NPD5210	Approved
0.6195	Remote Similarity	NPD4629	Approved
0.619	Remote Similarity	NPD4790	Discontinued
0.6183	Remote Similarity	NPD6033	Approved
0.6182	Remote Similarity	NPD5370	Suspended
0.6182	Remote Similarity	NPD4753	Phase 2
0.6172	Remote Similarity	NPD8080	Discontinued
0.6168	Remote Similarity	NPD4786	Approved
0.616	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.616	Remote Similarity	NPD7500	Approved
0.6154	Remote Similarity	NPD7632	Discontinued
0.6154	Remote Similarity	NPD5211	Phase 2
0.6148	Remote Similarity	NPD8415	Approved
0.6148	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6132	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6132	Remote Similarity	NPD3667	Approved
0.6121	Remote Similarity	NPD5285	Approved
0.6121	Remote Similarity	NPD5286	Approved
0.6121	Remote Similarity	NPD4696	Approved
0.6111	Remote Similarity	NPD7641	Discontinued
0.6106	Remote Similarity	NPD7748	Approved
0.6103	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD4755	Approved
0.6071	Remote Similarity	NPD5284	Approved
0.6071	Remote Similarity	NPD7515	Phase 2
0.6071	Remote Similarity	NPD5281	Approved
0.6063	Remote Similarity	NPD7100	Approved
0.6063	Remote Similarity	NPD7101	Approved
0.6063	Remote Similarity	NPD4522	Approved
0.6055	Remote Similarity	NPD7334	Approved
0.6055	Remote Similarity	NPD6409	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