NPASS Compound

Structure

NPC474393 OpenBabel07101719132D 40 42 0 0 1 0 0 0 0 0999 V2000 5.5298 -4.1060 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9800 -5.2952 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1210 -4.2039 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6033 -4.2039 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0176 -2.7638 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3127 0.7584 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2682 -0.8757 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9879 1.8869 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1397 1.4491 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1285 2.3248 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6274 -3.7322 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8637 -1.3813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3813 -1.3813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8525 -4.3268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2528 -3.3015 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.2295 -3.3015 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.1152 -2.3900 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9202 -1.6341 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4379 -1.6341 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1165 -0.4379 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6341 -0.4379 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2295 -0.9435 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2528 -0.9435 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4823 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4379 -2.6109 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.9202 -2.6109 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4258 0.2528 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9435 0.2528 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9501 -3.9530 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9877 -1.4217 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7917 0.6907 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1752 -4.5476 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0599 -0.1851 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5776 -0.1851 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6786 1.1963 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1963 1.1963 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3813 1.3813 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3403 -2.9847 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8226 -2.9847 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 11 1 0 0 0 0 2 14 1 0 0 0 0 5 17 1 0 0 0 0 6 34 1 0 0 0 0 7 35 1 0 0 0 0 8 36 1 0 0 0 0 9 37 1 0 0 0 0 10 38 1 0 0 0 0 11 14 2 0 0 0 0 12 18 2 0 0 0 0 12 20 1 0 0 0 0 13 19 2 0 0 0 0 13 21 1 0 0 0 0 14 30 1 0 0 0 0 15 3 1 1 0 0 0 15 16 1 0 0 0 0 15 25 1 0 0 0 0 16 4 1 1 0 0 0 16 26 1 0 0 0 0 17 31 2 0 0 0 0 17 39 1 0 0 0 0 18 22 1 0 0 0 0 18 26 1 0 0 0 0 19 23 1 0 0 0 0 19 25 1 0 0 0 0 20 27 2 0 0 0 0 20 34 1 0 0 0 0 21 28 2 0 0 0 0 21 35 1 0 0 0 0 22 23 1 0 0 0 0 22 24 2 0 0 0 0 23 29 2 0 0 0 0 24 27 1 0 0 0 0 24 32 1 0 0 0 0 25 39 1 6 0 0 0 26 40 1 1 0 0 0 27 36 1 0 0 0 0 28 29 1 0 0 0 0 28 37 1 0 0 0 0 29 38 1 0 0 0 0 30 33 2 0 0 0 0 30 40 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	558.25
Volume:	565.941
LogP:	3.879
LogD:	3.236
LogS:	-4.58
# Rotatable Bonds:	10
TPSA:	118.98
# H-Bond Aceptor:	10
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.327
Synthetic Accessibility Score:	4.252
Fsp3:	0.467
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.744
MDCK Permeability:	2.366447552049067e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.035
20% Bioavailability (F20%):	0.0
30% Bioavailability (F30%):	0.078

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.032
Plasma Protein Binding (PPB):	64.82369232177734%
Volume Distribution (VD):	0.806
Pgp-substrate:	27.36029624938965%

ADMET: Metabolism

CYP1A2-inhibitor:	0.021
CYP1A2-substrate:	0.971
CYP2C19-inhibitor:	0.81
CYP2C19-substrate:	0.938
CYP2C9-inhibitor:	0.897
CYP2C9-substrate:	0.639
CYP2D6-inhibitor:	0.046
CYP2D6-substrate:	0.396
CYP3A4-inhibitor:	0.716
CYP3A4-substrate:	0.922

ADMET: Excretion

Clearance (CL):	5.031
Half-life (T1/2):	0.167

ADMET: Toxicity

hERG Blockers:	0.342
Human Hepatotoxicity (H-HT):	0.088
Drug-inuced Liver Injury (DILI):	0.919
AMES Toxicity:	0.06
Rat Oral Acute Toxicity:	0.324
Maximum Recommended Daily Dose:	0.017
Skin Sensitization:	0.075
Carcinogencity:	0.016
Eye Corrosion:	0.003
Eye Irritation:	0.093
Respiratory Toxicity:	0.579

Download Data

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

Natural Product: NPC474393

Natural Product ID:	NPC474393
*Common Name:**	Kadangustin G
IUPAC Name:	n.a.
Synonyms:	Kadangustin G
Standard InCHIKey:	MLZWZUMLLVUXMT-HMCQAFCPSA-N
Standard InCHI:	InChI=1S/C30H38O10/c1-11-14(2)30(33)40-26-16(4)15(3)25(39-17(5)31)19-13-21(35-7)28(37-9)29(38-10)23(19)22-18(26)12-20(34-6)27(36-8)24(22)32/h11-13,15-16,25-26,32H,1-10H3/b14-11+/t15-,16+,25+,26+/m1/s1
SMILES:	C/C=C(/C(=O)O[C@H]1[C@@H](C)[C@@H](C)[C@H](OC(=O)C)c2c(c3c1cc(OC)c(c3O)OC)c(OC)c(c(c2)OC)OC)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL465863
PubChem CID:	24861900
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000238] Tannins [CHEMONTID:0001710] Hydrolyzable tannins

*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
NPO18146	Kadsura angustifolia	Species	Schisandraceae	Eukaryota	stems	Honghe Prefecture of Yunnan Province, China	2005-Oct	PMID[18278869]
NPO18146	Kadsura angustifolia	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21232955]
NPO18146	Kadsura angustifolia	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18146	Kadsura angustifolia	Species	Schisandraceae	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
EC50	1
Others	2

Activity Type	# Activity
Cell Line	1
Organism	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1452	Cell Line	C8166	Homo sapiens	CC50	=	72240.0	nM	PMID[493765]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	25730.0	nM	PMID[493765]
NPT2	Others	Unspecified		Ratio	=	2.81	n.a.	PMID[493765]

☑ 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 NPC474393 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	328
0.1-0.2	1349
0.2-0.3	3506
0.3-0.4	8239
0.4-0.5	10292
0.5-0.6	3670
0.6-0.7	6346
0.7-0.8	7482
0.8-0.85	1206
0.85-0.9	218
0.9-0.95	48
0.95-1	13

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC474347
0.993	High Similarity	NPC470916
0.9724	High Similarity	NPC149735
0.9718	High Similarity	NPC295297
0.9648	High Similarity	NPC474054
0.9645	High Similarity	NPC87883
0.9592	High Similarity	NPC476065
0.9589	High Similarity	NPC475141
0.9524	High Similarity	NPC473736
0.9517	High Similarity	NPC477381
0.9463	High Similarity	NPC475592
0.9452	High Similarity	NPC477379
0.9388	High Similarity	NPC471154
0.9324	High Similarity	NPC297271
0.9324	High Similarity	NPC126405
0.9324	High Similarity	NPC53669
0.9324	High Similarity	NPC77237
0.9324	High Similarity	NPC16791
0.9324	High Similarity	NPC308739
0.9324	High Similarity	NPC474606
0.9324	High Similarity	NPC217708
0.9324	High Similarity	NPC24562
0.932	High Similarity	NPC475756
0.931	High Similarity	NPC183083
0.931	High Similarity	NPC137352
0.9291	High Similarity	NPC471183
0.9272	High Similarity	NPC230531
0.9272	High Similarity	NPC215400
0.9247	High Similarity	NPC477879
0.922	High Similarity	NPC865
0.9216	High Similarity	NPC473445
0.9216	High Similarity	NPC42797
0.92	High Similarity	NPC238834
0.9189	High Similarity	NPC224472
0.9156	High Similarity	NPC291977
0.9149	High Similarity	NPC133025
0.9139	High Similarity	NPC473323
0.9133	High Similarity	NPC198461
0.9133	High Similarity	NPC312763
0.9116	High Similarity	NPC477375
0.9116	High Similarity	NPC198129
0.9116	High Similarity	NPC327352
0.9116	High Similarity	NPC252281
0.9085	High Similarity	NPC301765
0.9085	High Similarity	NPC156948
0.9085	High Similarity	NPC46277
0.9085	High Similarity	NPC3072
0.9085	High Similarity	NPC86605
0.9054	High Similarity	NPC322426
0.9054	High Similarity	NPC477376
0.9054	High Similarity	NPC477374
0.9034	High Similarity	NPC469630
0.9013	High Similarity	NPC469474
0.9007	High Similarity	NPC188378
0.9007	High Similarity	NPC7515
0.9007	High Similarity	NPC276026
0.9007	High Similarity	NPC56764
0.9007	High Similarity	NPC289258
0.9007	High Similarity	NPC555
0.9007	High Similarity	NPC206737
0.9007	High Similarity	NPC469659
0.8993	High Similarity	NPC316989
0.8986	High Similarity	NPC252402
0.8986	High Similarity	NPC316676
0.8986	High Similarity	NPC102934
0.8986	High Similarity	NPC325720
0.8944	High Similarity	NPC240279
0.8944	High Similarity	NPC214853
0.8944	High Similarity	NPC55239
0.8944	High Similarity	NPC180602
0.8926	High Similarity	NPC85141
0.8919	High Similarity	NPC178129
0.8912	High Similarity	NPC327651
0.8912	High Similarity	NPC318286
0.8882	High Similarity	NPC473425
0.8867	High Similarity	NPC473989
0.8861	High Similarity	NPC311912
0.8851	High Similarity	NPC321696
0.8851	High Similarity	NPC321958
0.8846	High Similarity	NPC249070
0.8844	High Similarity	NPC73467
0.8844	High Similarity	NPC121661
0.8844	High Similarity	NPC326144
0.8816	High Similarity	NPC477377
0.8805	High Similarity	NPC88557
0.8794	High Similarity	NPC184928
0.8794	High Similarity	NPC141493
0.8784	High Similarity	NPC110763
0.8784	High Similarity	NPC189239
0.8784	High Similarity	NPC197352
0.8784	High Similarity	NPC166506
0.8776	High Similarity	NPC76415
0.8776	High Similarity	NPC218510
0.8766	High Similarity	NPC29727
0.875	High Similarity	NPC475229
0.875	High Similarity	NPC476434
0.875	High Similarity	NPC272566
0.875	High Similarity	NPC477378
0.8742	High Similarity	NPC24425
0.8741	High Similarity	NPC135127
0.8733	High Similarity	NPC187398
0.8733	High Similarity	NPC476348
0.8732	High Similarity	NPC102256
0.8725	High Similarity	NPC154971
0.8725	High Similarity	NPC40222
0.8725	High Similarity	NPC268515
0.8725	High Similarity	NPC252286
0.8718	High Similarity	NPC24627
0.871	High Similarity	NPC125495
0.8707	High Similarity	NPC184684
0.8707	High Similarity	NPC67467
0.8707	High Similarity	NPC184641
0.8707	High Similarity	NPC133934
0.8701	High Similarity	NPC476642
0.8693	High Similarity	NPC65591
0.8693	High Similarity	NPC178574
0.869	High Similarity	NPC281780
0.8679	High Similarity	NPC83049
0.8679	High Similarity	NPC118162
0.8679	High Similarity	NPC320471
0.8675	High Similarity	NPC176903
0.8675	High Similarity	NPC30688
0.8671	High Similarity	NPC469518
0.8671	High Similarity	NPC469475
0.8667	High Similarity	NPC476347
0.8658	High Similarity	NPC477702
0.8658	High Similarity	NPC163898
0.8654	High Similarity	NPC328122
0.8649	High Similarity	NPC324962
0.8649	High Similarity	NPC477697
0.8649	High Similarity	NPC6568
0.8649	High Similarity	NPC477696
0.8649	High Similarity	NPC470811
0.8645	High Similarity	NPC477380
0.8636	High Similarity	NPC178195
0.8636	High Similarity	NPC348849
0.863	High Similarity	NPC114171
0.863	High Similarity	NPC230124
0.863	High Similarity	NPC6300
0.8621	High Similarity	NPC471988
0.8621	High Similarity	NPC471719
0.8618	High Similarity	NPC120426
0.8618	High Similarity	NPC21184
0.8618	High Similarity	NPC294522
0.8618	High Similarity	NPC205727
0.8611	High Similarity	NPC326095
0.8611	High Similarity	NPC244983
0.8611	High Similarity	NPC67247
0.8609	High Similarity	NPC236166
0.8609	High Similarity	NPC473408
0.8608	High Similarity	NPC469512
0.8601	High Similarity	NPC175067
0.8601	High Similarity	NPC204215
0.86	High Similarity	NPC212890
0.8592	High Similarity	NPC126836
0.8591	High Similarity	NPC16353
0.859	High Similarity	NPC477885
0.8582	High Similarity	NPC283114
0.8582	High Similarity	NPC207702
0.8582	High Similarity	NPC149008
0.8581	High Similarity	NPC469564
0.8581	High Similarity	NPC131971
0.8581	High Similarity	NPC229172
0.8581	High Similarity	NPC36531
0.8581	High Similarity	NPC470917
0.8581	High Similarity	NPC103637
0.8581	High Similarity	NPC230538
0.8571	High Similarity	NPC267291
0.8571	High Similarity	NPC109240
0.8571	High Similarity	NPC470769
0.8562	High Similarity	NPC105493
0.8553	High Similarity	NPC125570
0.8553	High Similarity	NPC106138
0.8553	High Similarity	NPC475250
0.8552	High Similarity	NPC165155
0.8552	High Similarity	NPC256262
0.8552	High Similarity	NPC24490
0.8552	High Similarity	NPC141765
0.8552	High Similarity	NPC34103
0.8542	High Similarity	NPC32778
0.8542	High Similarity	NPC158331
0.8533	High Similarity	NPC475868
0.8531	High Similarity	NPC474017
0.8531	High Similarity	NPC470095
0.8531	High Similarity	NPC470096
0.8526	High Similarity	NPC227062
0.8523	High Similarity	NPC34245
0.8523	High Similarity	NPC91492
0.8523	High Similarity	NPC256555
0.8523	High Similarity	NPC273657
0.8523	High Similarity	NPC106920
0.8523	High Similarity	NPC7439
0.8523	High Similarity	NPC110067
0.8516	High Similarity	NPC197188
0.8516	High Similarity	NPC43872
0.8516	High Similarity	NPC291510
0.8516	High Similarity	NPC116850
0.8516	High Similarity	NPC7178
0.8516	High Similarity	NPC238672
0.8516	High Similarity	NPC144801

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 NPC474393 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	285
0.1-0.2	877
0.2-0.3	1824
0.3-0.4	2674
0.4-0.5	1771
0.5-0.6	995
0.6-0.7	576
0.7-0.8	137
0.8-0.85	11
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8418	Intermediate Similarity	NPD6234	Discontinued
0.8392	Intermediate Similarity	NPD3027	Phase 3
0.8291	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8217	Intermediate Similarity	NPD37	Approved
0.8176	Intermediate Similarity	NPD4966	Approved
0.8176	Intermediate Similarity	NPD4965	Approved
0.8176	Intermediate Similarity	NPD4967	Phase 2
0.8171	Intermediate Similarity	NPD7228	Approved
0.8165	Intermediate Similarity	NPD1465	Phase 2
0.811	Intermediate Similarity	NPD7473	Discontinued
0.8095	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8095	Intermediate Similarity	NPD1613	Approved
0.8077	Intermediate Similarity	NPD1653	Approved
0.8037	Intermediate Similarity	NPD6232	Discontinued
0.8012	Intermediate Similarity	NPD5844	Phase 1
0.8	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD1934	Approved
0.7945	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD7266	Discontinued
0.7866	Intermediate Similarity	NPD7199	Phase 2
0.7852	Intermediate Similarity	NPD4060	Phase 1
0.7826	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD3817	Phase 2
0.7771	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7751	Intermediate Similarity	NPD7074	Phase 3
0.7738	Intermediate Similarity	NPD3818	Discontinued
0.773	Intermediate Similarity	NPD3882	Suspended
0.7727	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7725	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7725	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7725	Intermediate Similarity	NPD6166	Phase 2
0.7724	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7716	Intermediate Similarity	NPD2801	Approved
0.7716	Intermediate Similarity	NPD7819	Suspended
0.7706	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD7054	Approved
0.7688	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD7075	Discontinued
0.7682	Intermediate Similarity	NPD230	Phase 1
0.7661	Intermediate Similarity	NPD7240	Approved
0.7647	Intermediate Similarity	NPD7472	Approved
0.7628	Intermediate Similarity	NPD3750	Approved
0.7628	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD4908	Phase 1
0.758	Intermediate Similarity	NPD6190	Approved
0.7557	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD4380	Phase 2
0.7517	Intermediate Similarity	NPD3018	Phase 2
0.7514	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD1511	Approved
0.7483	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7466	Intermediate Similarity	NPD422	Phase 1
0.7466	Intermediate Similarity	NPD1610	Phase 2
0.7457	Intermediate Similarity	NPD7251	Discontinued
0.7453	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD6674	Discontinued
0.7451	Intermediate Similarity	NPD6355	Discontinued
0.744	Intermediate Similarity	NPD8127	Discontinued
0.7438	Intermediate Similarity	NPD2534	Approved
0.7438	Intermediate Similarity	NPD2533	Approved
0.7438	Intermediate Similarity	NPD2532	Approved
0.7436	Intermediate Similarity	NPD5763	Approved
0.7436	Intermediate Similarity	NPD5762	Approved
0.7429	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD4625	Phase 3
0.7414	Intermediate Similarity	NPD7549	Discontinued
0.7414	Intermediate Similarity	NPD7808	Phase 3
0.741	Intermediate Similarity	NPD7768	Phase 2
0.7405	Intermediate Similarity	NPD4628	Phase 3
0.7399	Intermediate Similarity	NPD6797	Phase 2
0.7391	Intermediate Similarity	NPD1512	Approved
0.7391	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD3620	Phase 2
0.7386	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD5494	Approved
0.7375	Intermediate Similarity	NPD6799	Approved
0.7375	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD2935	Discontinued
0.7365	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD2982	Phase 2
0.7365	Intermediate Similarity	NPD2983	Phase 2
0.7356	Intermediate Similarity	NPD7685	Pre-registration
0.7356	Intermediate Similarity	NPD6559	Discontinued
0.7349	Intermediate Similarity	NPD5402	Approved
0.7347	Intermediate Similarity	NPD3705	Approved
0.7342	Intermediate Similarity	NPD1652	Phase 2
0.7338	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD5124	Phase 1
0.7337	Intermediate Similarity	NPD6959	Discontinued
0.7333	Intermediate Similarity	NPD6801	Discontinued
0.7333	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD4626	Approved
0.7324	Intermediate Similarity	NPD5283	Phase 1
0.7322	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD6599	Discontinued
0.7308	Intermediate Similarity	NPD3748	Approved
0.7297	Intermediate Similarity	NPD2981	Phase 2
0.7296	Intermediate Similarity	NPD8166	Discontinued
0.7294	Intermediate Similarity	NPD7229	Phase 3
0.7285	Intermediate Similarity	NPD2861	Phase 2
0.7267	Intermediate Similarity	NPD4357	Discontinued
0.7262	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD2438	Suspended
0.7261	Intermediate Similarity	NPD6100	Approved
0.7261	Intermediate Similarity	NPD6099	Approved
0.726	Intermediate Similarity	NPD5691	Approved
0.7255	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD4749	Approved
0.7246	Intermediate Similarity	NPD5353	Approved
0.7246	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD5536	Phase 2
0.7239	Intermediate Similarity	NPD5403	Approved
0.7207	Intermediate Similarity	NPD6843	Phase 3
0.7207	Intermediate Similarity	NPD6842	Approved
0.7207	Intermediate Similarity	NPD6841	Approved
0.7197	Intermediate Similarity	NPD1510	Phase 2
0.7192	Intermediate Similarity	NPD1548	Phase 1
0.719	Intermediate Similarity	NPD7095	Approved
0.7188	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD4110	Phase 3
0.7183	Intermediate Similarity	NPD228	Approved
0.717	Intermediate Similarity	NPD1549	Phase 2
0.7169	Intermediate Similarity	NPD5090	Approved
0.7169	Intermediate Similarity	NPD7411	Suspended
0.7169	Intermediate Similarity	NPD5089	Approved
0.7169	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7166	Intermediate Similarity	NPD7680	Approved
0.7161	Intermediate Similarity	NPD1240	Approved
0.7152	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD2797	Approved
0.7152	Intermediate Similarity	NPD1551	Phase 2
0.7151	Intermediate Similarity	NPD5242	Approved
0.7143	Intermediate Similarity	NPD6798	Discontinued
0.7133	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD3751	Discontinued
0.7125	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD919	Approved
0.7117	Intermediate Similarity	NPD5401	Approved
0.7117	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD447	Suspended
0.711	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7088	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD1283	Approved
0.7083	Intermediate Similarity	NPD8455	Phase 2
0.7079	Intermediate Similarity	NPD8313	Approved
0.7079	Intermediate Similarity	NPD8312	Approved
0.707	Intermediate Similarity	NPD1607	Approved
0.707	Intermediate Similarity	NPD6653	Approved
0.7059	Intermediate Similarity	NPD3749	Approved
0.7056	Intermediate Similarity	NPD8434	Phase 2
0.7052	Intermediate Similarity	NPD3926	Phase 2
0.7051	Intermediate Similarity	NPD2979	Phase 3
0.7051	Intermediate Similarity	NPD943	Approved
0.7048	Intermediate Similarity	NPD4005	Discontinued
0.7047	Intermediate Similarity	NPD3496	Discontinued
0.7044	Intermediate Similarity	NPD2796	Approved
0.7042	Intermediate Similarity	NPD3021	Approved
0.7042	Intermediate Similarity	NPD3022	Approved
0.7037	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD3268	Approved
0.7025	Intermediate Similarity	NPD7097	Phase 1
0.7019	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3540	Phase 1
0.6994	Remote Similarity	NPD3787	Discontinued
0.6987	Remote Similarity	NPD6233	Phase 2
0.6979	Remote Similarity	NPD8151	Discontinued
0.6975	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD7003	Approved
0.6964	Remote Similarity	NPD6386	Approved
0.6964	Remote Similarity	NPD6385	Approved
0.6959	Remote Similarity	NPD4055	Discovery
0.6954	Remote Similarity	NPD1608	Approved
0.6954	Remote Similarity	NPD9269	Phase 2
0.6948	Remote Similarity	NPD9494	Approved
0.6946	Remote Similarity	NPD6055	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD3226	Approved
0.6943	Remote Similarity	NPD4140	Approved
0.6941	Remote Similarity	NPD6374	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD3539	Phase 1
0.6937	Remote Similarity	NPD6032	Approved
0.6923	Remote Similarity	NPD3764	Approved
0.6909	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD6832	Phase 2
0.6901	Remote Similarity	NPD1358	Approved
0.6899	Remote Similarity	NPD4340	Discontinued
0.6897	Remote Similarity	NPD5711	Approved
0.6897	Remote Similarity	NPD5710	Approved
0.689	Remote Similarity	NPD6666	Approved
0.689	Remote Similarity	NPD6667	Approved
0.689	Remote Similarity	NPD7124	Phase 2

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