NPASS Compound

Structure

NPC474421 OpenBabel07101718302D 37 40 0 0 1 0 0 0 0 0999 V2000 -3.2741 2.8557 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6898 6.0840 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3462 -0.3726 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1372 -1.7825 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0036 1.8292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0135 0.2459 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7754 -1.4609 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3462 2.5542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5013 3.0420 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7728 3.3435 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3462 1.5786 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3462 2.5542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6898 5.1084 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1911 0.1152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8330 -1.6805 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8449 3.6449 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.3462 1.5786 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7728 0.7893 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6564 1.5786 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0830 3.3435 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0830 0.7893 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7728 -0.7893 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6564 2.5542 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5013 1.0908 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8449 -0.4878 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8449 0.4878 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5347 4.6206 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0360 -0.3726 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4065 -2.4698 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6564 4.1327 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0742 -1.7171 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9891 0.2459 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8449 4.6206 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1911 1.0908 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2299 -0.7893 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3462 -0.0000 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 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 7 25 1 0 0 0 0 8 9 2 0 0 0 0 8 17 1 0 0 0 0 9 23 1 0 0 0 0 10 12 1 0 0 0 0 10 16 1 0 0 0 0 11 12 2 0 0 0 0 11 18 1 0 0 0 0 13 27 2 0 0 0 0 13 33 1 0 0 0 0 14 28 2 0 0 0 0 14 34 1 0 0 0 0 15 29 2 0 0 0 0 15 35 1 0 0 0 0 16 20 1 0 0 0 0 16 33 1 1 0 0 0 17 24 1 1 0 0 0 17 34 1 0 0 0 0 18 26 1 1 0 0 0 18 36 1 0 0 0 0 19 21 1 0 0 0 0 19 23 1 6 0 0 0 19 24 1 0 0 0 0 20 23 1 1 0 0 0 20 30 1 0 0 0 0 21 26 1 6 0 0 0 21 35 1 0 0 0 0 22 25 1 0 0 0 0 22 31 2 0 0 0 0 22 36 1 0 0 0 0 23 5 1 6 0 0 0 24 6 1 6 0 0 0 24 32 1 0 0 0 0 25 26 1 6 0 0 0 25 37 1 0 0 0 0 26 37 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	522.21
Volume:	504.9
LogP:	1.842
LogD:	0.518
LogS:	-3.875
# Rotatable Bonds:	6
TPSA:	158.19
# H-Bond Aceptor:	11
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.235
Synthetic Accessibility Score:	6.224
Fsp3:	0.692
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:	-5.35
MDCK Permeability:	0.0001256022951565683
Pgp-inhibitor:	0.996
Pgp-substrate:	0.397
Human Intestinal Absorption (HIA):	0.252
20% Bioavailability (F20%):	0.922
30% Bioavailability (F30%):	0.991

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.475
Plasma Protein Binding (PPB):	33.88678741455078%
Volume Distribution (VD):	1.208
Pgp-substrate:	52.00960159301758%

ADMET: Metabolism

CYP1A2-inhibitor:	0.006
CYP1A2-substrate:	0.07
CYP2C19-inhibitor:	0.013
CYP2C19-substrate:	0.128
CYP2C9-inhibitor:	0.001
CYP2C9-substrate:	0.011
CYP2D6-inhibitor:	0.017
CYP2D6-substrate:	0.067
CYP3A4-inhibitor:	0.586
CYP3A4-substrate:	0.322

ADMET: Excretion

Clearance (CL):	2.407
Half-life (T1/2):	0.609

ADMET: Toxicity

hERG Blockers:	0.044
Human Hepatotoxicity (H-HT):	0.931
Drug-inuced Liver Injury (DILI):	0.847
AMES Toxicity:	0.486
Rat Oral Acute Toxicity:	0.893
Maximum Recommended Daily Dose:	0.012
Skin Sensitization:	0.537
Carcinogencity:	0.475
Eye Corrosion:	0.007
Eye Irritation:	0.014
Respiratory Toxicity:	0.971

Download Data

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

Natural Product: NPC474421

Natural Product ID:	NPC474421
*Common Name:**	Brianodin A
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	VTOQVTKIZWJWGX-IUTLRFKRSA-N
Standard InCHI:	InChI=1S/C26H34O11/c1-12-10-16(33-13(2)27)20(30)23(5)9-8-17(34-14(3)28)24(6,32)19(23)21(35-15(4)29)26-18(11-12)36-22(31)25(26,7)37-26/h8-9,11,16-21,30,32H,10H2,1-7H3/b12-11-/t16-,17-,18+,19-,20-,21+,23+,24-,25+,26+/m1/s1
SMILES:	CC1=CC2C3(C(C4C(C=CC(C4(C)O)OC(=O)C)(C(C(C1)OC(=O)C)O)C)OC(=O)C)C(O3)(C(=O)O2)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL467942
PubChem CID:	24862285
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	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	=	4.3	ug.mL-1	PMID[469158]
NPT137	Cell Line	L1210	Mus musculus	IC50	=	1.8	ug.mL-1	PMID[469158]

☑ 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 NPC474421 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	218
0.1-0.2	1314
0.2-0.3	4614
0.3-0.4	9354
0.4-0.5	13330
0.5-0.6	7740
0.6-0.7	4840
0.7-0.8	1116
0.8-0.85	122
0.85-0.9	23
0.9-0.95	8
0.95-1	18

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC326994
1.0	High Similarity	NPC72813
1.0	High Similarity	NPC324327
1.0	High Similarity	NPC194620
0.9899	High Similarity	NPC14862
0.9899	High Similarity	NPC474664
0.9899	High Similarity	NPC327286
0.9899	High Similarity	NPC169888
0.9899	High Similarity	NPC55972
0.9899	High Similarity	NPC233379
0.9898	High Similarity	NPC9303
0.9898	High Similarity	NPC16313
0.98	High Similarity	NPC15218
0.9697	High Similarity	NPC475802
0.9694	High Similarity	NPC4620
0.9604	High Similarity	NPC475922
0.9596	High Similarity	NPC475676
0.9596	High Similarity	NPC220964
0.951	High Similarity	NPC115257
0.951	High Similarity	NPC161816
0.9143	High Similarity	NPC473877
0.9109	High Similarity	NPC19239
0.9109	High Similarity	NPC474165
0.9109	High Similarity	NPC474166
0.9109	High Similarity	NPC69171
0.901	High Similarity	NPC183571
0.8889	High Similarity	NPC474333
0.8857	High Similarity	NPC42662
0.8824	High Similarity	NPC471148
0.8807	High Similarity	NPC296822
0.8762	High Similarity	NPC94377
0.8725	High Similarity	NPC164598
0.8725	High Similarity	NPC474339
0.8667	High Similarity	NPC475587
0.8667	High Similarity	NPC475510
0.8667	High Similarity	NPC477513
0.8654	High Similarity	NPC472756
0.8641	High Similarity	NPC472754
0.8627	High Similarity	NPC475949
0.8611	High Similarity	NPC317687
0.8598	High Similarity	NPC281624
0.8585	High Similarity	NPC473595
0.8585	High Similarity	NPC473939
0.8544	High Similarity	NPC472753
0.8519	High Similarity	NPC317107
0.8468	Intermediate Similarity	NPC476712
0.8468	Intermediate Similarity	NPC476713
0.8462	Intermediate Similarity	NPC149371
0.8455	Intermediate Similarity	NPC73314
0.8431	Intermediate Similarity	NPC471140
0.8426	Intermediate Similarity	NPC473594
0.8426	Intermediate Similarity	NPC474586
0.8426	Intermediate Similarity	NPC473975
0.8426	Intermediate Similarity	NPC473843
0.8381	Intermediate Similarity	NPC472755
0.8378	Intermediate Similarity	NPC476711
0.8378	Intermediate Similarity	NPC476710
0.8365	Intermediate Similarity	NPC47880
0.835	Intermediate Similarity	NPC471144
0.8349	Intermediate Similarity	NPC194619
0.8333	Intermediate Similarity	NPC473859
0.8333	Intermediate Similarity	NPC230800
0.8333	Intermediate Similarity	NPC279621
0.8302	Intermediate Similarity	NPC472748
0.8302	Intermediate Similarity	NPC474741
0.8269	Intermediate Similarity	NPC288876
0.8241	Intermediate Similarity	NPC322903
0.8235	Intermediate Similarity	NPC475659
0.8224	Intermediate Similarity	NPC472749
0.8224	Intermediate Similarity	NPC472751
0.8208	Intermediate Similarity	NPC472747
0.8208	Intermediate Similarity	NPC472750
0.8208	Intermediate Similarity	NPC475945
0.8208	Intermediate Similarity	NPC475871
0.819	Intermediate Similarity	NPC201718
0.819	Intermediate Similarity	NPC264477
0.819	Intermediate Similarity	NPC477511
0.8173	Intermediate Similarity	NPC222303
0.8163	Intermediate Similarity	NPC478112
0.8158	Intermediate Similarity	NPC470186
0.8155	Intermediate Similarity	NPC17585
0.8155	Intermediate Similarity	NPC476315
0.8142	Intermediate Similarity	NPC471146
0.8137	Intermediate Similarity	NPC474247
0.8131	Intermediate Similarity	NPC471143
0.8131	Intermediate Similarity	NPC258532
0.8131	Intermediate Similarity	NPC477510
0.8113	Intermediate Similarity	NPC474747
0.81	Intermediate Similarity	NPC475971
0.8095	Intermediate Similarity	NPC477512
0.8091	Intermediate Similarity	NPC5103
0.807	Intermediate Similarity	NPC475130
0.807	Intermediate Similarity	NPC475401
0.807	Intermediate Similarity	NPC474286
0.8058	Intermediate Similarity	NPC107476
0.8058	Intermediate Similarity	NPC471141
0.8058	Intermediate Similarity	NPC14961
0.8058	Intermediate Similarity	NPC270013
0.8058	Intermediate Similarity	NPC36954
0.8053	Intermediate Similarity	NPC270478
0.8039	Intermediate Similarity	NPC212486
0.8039	Intermediate Similarity	NPC228451
0.8039	Intermediate Similarity	NPC125674
0.8039	Intermediate Similarity	NPC475838
0.8039	Intermediate Similarity	NPC476300
0.8036	Intermediate Similarity	NPC477126
0.8036	Intermediate Similarity	NPC469454
0.8036	Intermediate Similarity	NPC469463
0.8036	Intermediate Similarity	NPC469496
0.8019	Intermediate Similarity	NPC474742
0.8019	Intermediate Similarity	NPC476270
0.8	Intermediate Similarity	NPC161855
0.8	Intermediate Similarity	NPC473326
0.8	Intermediate Similarity	NPC477092
0.7982	Intermediate Similarity	NPC475305
0.7982	Intermediate Similarity	NPC26617
0.7982	Intermediate Similarity	NPC473590
0.7981	Intermediate Similarity	NPC76862
0.7981	Intermediate Similarity	NPC158416
0.7981	Intermediate Similarity	NPC470883
0.7981	Intermediate Similarity	NPC54731
0.7981	Intermediate Similarity	NPC39859
0.7963	Intermediate Similarity	NPC296950
0.7963	Intermediate Similarity	NPC146731
0.7963	Intermediate Similarity	NPC203659
0.7961	Intermediate Similarity	NPC81386
0.7961	Intermediate Similarity	NPC303942
0.7961	Intermediate Similarity	NPC57405
0.7961	Intermediate Similarity	NPC474035
0.7949	Intermediate Similarity	NPC188222
0.7949	Intermediate Similarity	NPC310035
0.7949	Intermediate Similarity	NPC282003
0.7944	Intermediate Similarity	NPC324017
0.7944	Intermediate Similarity	NPC105725
0.7944	Intermediate Similarity	NPC320019
0.7944	Intermediate Similarity	NPC474709
0.7941	Intermediate Similarity	NPC30515
0.7941	Intermediate Similarity	NPC184463
0.7931	Intermediate Similarity	NPC475003
0.7909	Intermediate Similarity	NPC308191
0.7905	Intermediate Similarity	NPC40812
0.79	Intermediate Similarity	NPC266957
0.789	Intermediate Similarity	NPC179891
0.7885	Intermediate Similarity	NPC471142
0.7881	Intermediate Similarity	NPC303006
0.7881	Intermediate Similarity	NPC67251
0.7876	Intermediate Similarity	NPC101400
0.7876	Intermediate Similarity	NPC101965
0.787	Intermediate Similarity	NPC110989
0.787	Intermediate Similarity	NPC475321
0.787	Intermediate Similarity	NPC232515
0.787	Intermediate Similarity	NPC260809
0.787	Intermediate Similarity	NPC474783
0.7869	Intermediate Similarity	NPC470185
0.7864	Intermediate Similarity	NPC475912
0.7857	Intermediate Similarity	NPC179798
0.7857	Intermediate Similarity	NPC304180
0.7857	Intermediate Similarity	NPC287311
0.7857	Intermediate Similarity	NPC231601
0.785	Intermediate Similarity	NPC15993
0.785	Intermediate Similarity	NPC473332
0.7843	Intermediate Similarity	NPC65359
0.7843	Intermediate Similarity	NPC474232
0.7843	Intermediate Similarity	NPC475748
0.7843	Intermediate Similarity	NPC51004
0.7843	Intermediate Similarity	NPC469368
0.7843	Intermediate Similarity	NPC475855
0.7838	Intermediate Similarity	NPC477102
0.7826	Intermediate Similarity	NPC471145
0.7826	Intermediate Similarity	NPC469684
0.7822	Intermediate Similarity	NPC287089
0.7822	Intermediate Similarity	NPC476803
0.7818	Intermediate Similarity	NPC266514
0.781	Intermediate Similarity	NPC473291
0.781	Intermediate Similarity	NPC476009
0.78	Intermediate Similarity	NPC278283
0.78	Intermediate Similarity	NPC50637
0.7797	Intermediate Similarity	NPC23786
0.7797	Intermediate Similarity	NPC470265
0.7788	Intermediate Similarity	NPC66108
0.7788	Intermediate Similarity	NPC313921
0.7788	Intermediate Similarity	NPC121825
0.7788	Intermediate Similarity	NPC190294
0.7788	Intermediate Similarity	NPC98038
0.7788	Intermediate Similarity	NPC471147
0.7778	Intermediate Similarity	NPC475986
0.7778	Intermediate Similarity	NPC473596
0.7778	Intermediate Similarity	NPC49393
0.7778	Intermediate Similarity	NPC283567
0.7778	Intermediate Similarity	NPC252242
0.7778	Intermediate Similarity	NPC39996
0.7778	Intermediate Similarity	NPC200672
0.7778	Intermediate Similarity	NPC475956
0.7778	Intermediate Similarity	NPC225353
0.7778	Intermediate Similarity	NPC214714
0.7768	Intermediate Similarity	NPC257240
0.7768	Intermediate Similarity	NPC475563
0.7768	Intermediate Similarity	NPC235014
0.7768	Intermediate Similarity	NPC472215
0.7768	Intermediate Similarity	NPC477103

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 NPC474421 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	1832
0.2-0.3	3689
0.3-0.4	2256
0.4-0.5	730
0.5-0.6	317
0.6-0.7	121
0.7-0.8	10
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
0.802	Intermediate Similarity	NPD6698	Approved
0.802	Intermediate Similarity	NPD46	Approved
0.7982	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7768	Intermediate Similarity	NPD6371	Approved
0.7699	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7596	Intermediate Similarity	NPD7983	Approved
0.75	Intermediate Similarity	NPD7838	Discovery
0.7453	Intermediate Similarity	NPD5282	Discontinued
0.7373	Intermediate Similarity	NPD7115	Discovery
0.7353	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7281	Intermediate Similarity	NPD6686	Approved
0.7273	Intermediate Similarity	NPD8513	Phase 3
0.7273	Intermediate Similarity	NPD8516	Approved
0.7273	Intermediate Similarity	NPD8515	Approved
0.7273	Intermediate Similarity	NPD8517	Approved
0.7222	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD5779	Approved
0.7196	Intermediate Similarity	NPD5778	Approved
0.7182	Intermediate Similarity	NPD4225	Approved
0.713	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD5344	Discontinued
0.7049	Intermediate Similarity	NPD6319	Approved
0.7009	Intermediate Similarity	NPD5785	Approved
0.7009	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD8074	Phase 3
0.6944	Remote Similarity	NPD6411	Approved
0.6916	Remote Similarity	NPD1695	Approved
0.6875	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD7492	Approved
0.6803	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD5369	Approved
0.6789	Remote Similarity	NPD7637	Suspended
0.6774	Remote Similarity	NPD6054	Approved
0.6772	Remote Similarity	NPD8273	Phase 1
0.6772	Remote Similarity	NPD6616	Approved
0.6767	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD6101	Approved
0.6752	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.675	Remote Similarity	NPD8297	Approved
0.6746	Remote Similarity	NPD8328	Phase 3
0.6731	Remote Similarity	NPD4269	Approved
0.6731	Remote Similarity	NPD4270	Approved
0.6729	Remote Similarity	NPD4250	Approved
0.6729	Remote Similarity	NPD4251	Approved
0.6719	Remote Similarity	NPD7078	Approved
0.6696	Remote Similarity	NPD7839	Suspended
0.6667	Remote Similarity	NPD6649	Approved
0.6667	Remote Similarity	NPD6648	Approved
0.6667	Remote Similarity	NPD6650	Approved
0.6667	Remote Similarity	NPD6370	Approved
0.6667	Remote Similarity	NPD7736	Approved
0.6667	Remote Similarity	NPD7154	Phase 3
0.664	Remote Similarity	NPD6059	Approved
0.6639	Remote Similarity	NPD6372	Approved
0.6639	Remote Similarity	NPD6373	Approved
0.6637	Remote Similarity	NPD6084	Phase 2
0.6637	Remote Similarity	NPD6083	Phase 2
0.6636	Remote Similarity	NPD5786	Approved
0.6636	Remote Similarity	NPD4249	Approved
0.6615	Remote Similarity	NPD7319	Approved
0.6614	Remote Similarity	NPD7642	Approved
0.6612	Remote Similarity	NPD6053	Discontinued
0.6589	Remote Similarity	NPD8293	Discontinued
0.6587	Remote Similarity	NPD6016	Approved
0.6587	Remote Similarity	NPD6921	Approved
0.6587	Remote Similarity	NPD6015	Approved
0.6579	Remote Similarity	NPD7638	Approved
0.6577	Remote Similarity	NPD6399	Phase 3
0.6557	Remote Similarity	NPD4632	Approved
0.6555	Remote Similarity	NPD6899	Approved
0.6555	Remote Similarity	NPD6881	Approved
0.6542	Remote Similarity	NPD1694	Approved
0.6542	Remote Similarity	NPD5363	Approved
0.6538	Remote Similarity	NPD4819	Approved
0.6538	Remote Similarity	NPD4822	Approved
0.6538	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD4821	Approved
0.6538	Remote Similarity	NPD4252	Approved
0.6538	Remote Similarity	NPD4820	Approved
0.6535	Remote Similarity	NPD5988	Approved
0.6525	Remote Similarity	NPD6402	Approved
0.6525	Remote Similarity	NPD5739	Approved
0.6525	Remote Similarity	NPD7128	Approved
0.6525	Remote Similarity	NPD6675	Approved
0.6522	Remote Similarity	NPD7640	Approved
0.6522	Remote Similarity	NPD7639	Approved
0.6515	Remote Similarity	NPD7260	Phase 2
0.6512	Remote Similarity	NPD7507	Approved
0.6512	Remote Similarity	NPD8451	Approved
0.6509	Remote Similarity	NPD5362	Discontinued
0.6509	Remote Similarity	NPD6110	Phase 1
0.6505	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD7604	Phase 2
0.6484	Remote Similarity	NPD7830	Approved
0.6484	Remote Similarity	NPD7829	Approved
0.6475	Remote Similarity	NPD6882	Approved
0.6471	Remote Similarity	NPD5697	Approved
0.6471	Remote Similarity	NPD6412	Phase 2
0.6462	Remote Similarity	NPD8448	Approved
0.646	Remote Similarity	NPD5695	Phase 3
0.6446	Remote Similarity	NPD6883	Approved
0.6446	Remote Similarity	NPD7290	Approved
0.6446	Remote Similarity	NPD7102	Approved
0.6435	Remote Similarity	NPD5696	Approved
0.6423	Remote Similarity	NPD8133	Approved
0.6417	Remote Similarity	NPD7320	Approved
0.6415	Remote Similarity	NPD6435	Approved
0.64	Remote Similarity	NPD6009	Approved
0.6393	Remote Similarity	NPD6617	Approved
0.6393	Remote Similarity	NPD8130	Phase 1
0.6393	Remote Similarity	NPD6847	Approved
0.6393	Remote Similarity	NPD6869	Approved
0.6389	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD6008	Approved
0.6373	Remote Similarity	NPD8039	Approved
0.6364	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD6014	Approved
0.6364	Remote Similarity	NPD6012	Approved
0.6364	Remote Similarity	NPD6013	Approved
0.6346	Remote Similarity	NPD4268	Approved
0.6346	Remote Similarity	NPD4271	Approved
0.6333	Remote Similarity	NPD5701	Approved
0.6328	Remote Similarity	NPD7503	Approved
0.6328	Remote Similarity	NPD8444	Approved
0.6328	Remote Similarity	NPD5983	Phase 2
0.6316	Remote Similarity	NPD8391	Approved
0.6316	Remote Similarity	NPD8390	Approved
0.6316	Remote Similarity	NPD8392	Approved
0.6311	Remote Similarity	NPD4634	Approved
0.6308	Remote Similarity	NPD8340	Approved
0.6308	Remote Similarity	NPD8342	Approved
0.6308	Remote Similarity	NPD8341	Approved
0.6308	Remote Similarity	NPD8299	Approved
0.6281	Remote Similarity	NPD6011	Approved
0.6273	Remote Similarity	NPD7524	Approved
0.6262	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD5209	Approved
0.6261	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.626	Remote Similarity	NPD2204	Approved
0.626	Remote Similarity	NPD6336	Discontinued
0.6226	Remote Similarity	NPD5368	Approved
0.6222	Remote Similarity	NPD6845	Suspended
0.622	Remote Similarity	NPD7328	Approved
0.622	Remote Similarity	NPD7327	Approved
0.6216	Remote Similarity	NPD6672	Approved
0.6216	Remote Similarity	NPD5737	Approved
0.6202	Remote Similarity	NPD8033	Approved
0.6202	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6195	Remote Similarity	NPD5693	Phase 1
0.6194	Remote Similarity	NPD5956	Approved
0.6179	Remote Similarity	NPD6421	Discontinued
0.6172	Remote Similarity	NPD7516	Approved
0.6165	Remote Similarity	NPD6033	Approved
0.6154	Remote Similarity	NPD8080	Discontinued
0.6147	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6147	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6131	Remote Similarity	NPD8415	Approved
0.6129	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6124	Remote Similarity	NPD8377	Approved
0.6124	Remote Similarity	NPD8294	Approved
0.6087	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.6077	Remote Similarity	NPD8380	Approved
0.6077	Remote Similarity	NPD8296	Approved
0.6077	Remote Similarity	NPD8335	Approved
0.6077	Remote Similarity	NPD8379	Approved
0.6077	Remote Similarity	NPD8378	Approved
0.6068	Remote Similarity	NPD7902	Approved
0.6055	Remote Similarity	NPD5332	Approved
0.6055	Remote Similarity	NPD6695	Phase 3
0.6055	Remote Similarity	NPD5331	Approved
0.6053	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.605	Remote Similarity	NPD1700	Approved
0.6047	Remote Similarity	NPD7100	Approved
0.6047	Remote Similarity	NPD7101	Approved
0.6036	Remote Similarity	NPD6098	Approved
0.6034	Remote Similarity	NPD4629	Approved
0.6034	Remote Similarity	NPD5210	Approved
0.6033	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.6033	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.602	Remote Similarity	NPD3197	Phase 1
0.6019	Remote Similarity	NPD4790	Discontinued
0.6018	Remote Similarity	NPD6080	Approved
0.6018	Remote Similarity	NPD6904	Approved
0.6018	Remote Similarity	NPD5370	Suspended
0.6018	Remote Similarity	NPD4753	Phase 2
0.6018	Remote Similarity	NPD6673	Approved
0.6016	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6016	Remote Similarity	NPD7500	Approved
0.6	Remote Similarity	NPD5211	Phase 2
0.6	Remote Similarity	NPD7632	Discontinued
0.6	Remote Similarity	NPD4786	Approved
0.5969	Remote Similarity	NPD7641	Discontinued
0.5969	Remote Similarity	NPD6335	Approved
0.5966	Remote Similarity	NPD5285	Approved
0.5966	Remote Similarity	NPD5286	Approved
0.5966	Remote Similarity	NPD4696	Approved
0.5963	Remote Similarity	NPD3667	Approved
0.5963	Remote Similarity	NPD4800	Clinical (unspecified phase)

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