NPASS Compound

Structure

CID113862 OpenBabel06191715472D 33 35 0 0 1 0 0 0 0 0999 V2000 2.4665 -4.3162 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4081 -4.0181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2564 2.0067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0067 2.0067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5145 -1.0929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8274 0.4897 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4216 1.1585 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1585 1.1585 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7734 -2.7734 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4897 -2.7734 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1045 -3.4423 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.7734 -1.8274 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4897 -1.8274 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1045 -1.1585 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1585 -1.1585 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6871 -1.5826 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4241 -1.5826 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3493 -0.2448 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9137 -0.2448 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9319 -0.6689 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6689 -0.6689 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2630 -0.0000 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 1.1585 -3.4423 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3560 -2.2515 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -1.0929 -2.2515 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 1.2820 -4.3801 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0115 1.0929 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2515 1.0929 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8456 -0.4241 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5826 -0.4241 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5079 0.9137 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2448 0.9137 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 11 1 0 0 0 0 3 28 1 0 0 0 0 4 29 1 0 0 0 0 5 30 1 0 0 0 0 6 31 1 0 0 0 0 7 32 1 0 0 0 0 8 33 1 0 0 0 0 9 11 1 0 0 0 0 9 12 1 0 0 0 0 10 13 1 0 0 0 0 10 24 1 0 0 0 0 11 24 1 6 0 0 0 12 14 2 0 0 0 0 12 16 1 0 0 0 0 13 15 2 0 0 0 0 13 17 1 0 0 0 0 14 15 1 0 0 0 0 14 18 1 0 0 0 0 15 19 1 0 0 0 0 16 20 2 0 0 0 0 16 25 1 0 0 0 0 17 21 2 0 0 0 0 17 26 1 0 0 0 0 18 22 2 0 0 0 0 18 28 1 0 0 0 0 19 23 2 0 0 0 0 19 29 1 0 0 0 0 20 22 1 0 0 0 0 20 30 1 0 0 0 0 21 23 1 0 0 0 0 21 31 1 0 0 0 0 22 32 1 0 0 0 0 23 33 1 0 0 0 0 24 2 1 6 0 0 0 24 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	588.04
Volume:	482.271
LogP:	5.152
LogD:	3.496
LogS:	-5.548
# Rotatable Bonds:	6
TPSA:	75.61
# H-Bond Aceptor:	7
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.482
Synthetic Accessibility Score:	3.935
Fsp3:	0.5
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:	-4.668
MDCK Permeability:	2.3301912733586505e-05
Pgp-inhibitor:	0.995
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.549
20% Bioavailability (F20%):	0.0
30% Bioavailability (F30%):	0.002

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.068
Plasma Protein Binding (PPB):	94.20624542236328%
Volume Distribution (VD):	0.625
Pgp-substrate:	7.814040660858154%

ADMET: Metabolism

CYP1A2-inhibitor:	0.083
CYP1A2-substrate:	0.995
CYP2C19-inhibitor:	0.849
CYP2C19-substrate:	0.928
CYP2C9-inhibitor:	0.368
CYP2C9-substrate:	0.897
CYP2D6-inhibitor:	0.0
CYP2D6-substrate:	0.874
CYP3A4-inhibitor:	0.562
CYP3A4-substrate:	0.905

ADMET: Excretion

Clearance (CL):	1.78
Half-life (T1/2):	0.065

ADMET: Toxicity

hERG Blockers:	0.411
Human Hepatotoxicity (H-HT):	0.052
Drug-inuced Liver Injury (DILI):	0.074
AMES Toxicity:	0.014
Rat Oral Acute Toxicity:	0.592
Maximum Recommended Daily Dose:	0.03
Skin Sensitization:	0.131
Carcinogencity:	0.024
Eye Corrosion:	0.003
Eye Irritation:	0.146
Respiratory Toxicity:	0.229

Download Data

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

Natural Product: NPC113862

Natural Product ID:	NPC113862
*Common Name:**	KMTKKULOWMDTND-BUBHHJDNSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	KMTKKULOWMDTND-BUBHHJDNSA-N
Standard InCHI:	InChI=1S/C24H30Br2O7/c1-11-9-12-14(18(28-3)22(32-7)20(30-5)16(12)25)15-13(10-24(11,2)27)17(26)21(31-6)23(33-8)19(15)29-4/h11,27H,9-10H2,1-8H3/t11-,24-/m0/s1
SMILES:	COc1c(OC)c2c3c(C[C@@H]([C@@](Cc2c(c1OC)Br)(C)O)C)c(Br)c(c(c3OC)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3237309
PubChem CID:	3001666
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
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16562834]
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	fruit	n.a.	PMID[24155209]
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24959987]
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25302569]
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8367	Fructus schiandrae	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8367	Fructus schiandrae	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO8187	Schisandra chinensis	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
Others	1

Activity Type	# Activity
CELL-LINE	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT21742	CELL-LINE	L02	Homo sapiens	Survival	=	54.2	%	PMID[526095]

☑ 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 NPC113862 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	552
0.1-0.2	2400
0.2-0.3	8624
0.3-0.4	12404
0.4-0.5	4700
0.5-0.6	10017
0.6-0.7	3510
0.7-0.8	486
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8138	Intermediate Similarity	NPC102256
0.8117	Intermediate Similarity	NPC152947
0.7973	Intermediate Similarity	NPC214853
0.7973	Intermediate Similarity	NPC180602
0.7973	Intermediate Similarity	NPC240279
0.7973	Intermediate Similarity	NPC55239
0.7905	Intermediate Similarity	NPC469659
0.7905	Intermediate Similarity	NPC56764
0.7905	Intermediate Similarity	NPC206737
0.7905	Intermediate Similarity	NPC7515
0.7905	Intermediate Similarity	NPC289258
0.7905	Intermediate Similarity	NPC188378
0.7905	Intermediate Similarity	NPC276026
0.7905	Intermediate Similarity	NPC555
0.7867	Intermediate Similarity	NPC168680
0.7862	Intermediate Similarity	NPC149008
0.7862	Intermediate Similarity	NPC283114
0.7862	Intermediate Similarity	NPC207702
0.7829	Intermediate Similarity	NPC89341
0.7815	Intermediate Similarity	NPC160932
0.7815	Intermediate Similarity	NPC53722
0.7815	Intermediate Similarity	NPC201404
0.7815	Intermediate Similarity	NPC290714
0.78	Intermediate Similarity	NPC133025
0.7792	Intermediate Similarity	NPC109346
0.7748	Intermediate Similarity	NPC3072
0.7748	Intermediate Similarity	NPC86605
0.7748	Intermediate Similarity	NPC46277
0.7748	Intermediate Similarity	NPC156948
0.7748	Intermediate Similarity	NPC301765
0.7703	Intermediate Similarity	NPC184928
0.7703	Intermediate Similarity	NPC141493
0.7697	Intermediate Similarity	NPC471183
0.7632	Intermediate Similarity	NPC156356
0.7607	Intermediate Similarity	NPC38980
0.76	Intermediate Similarity	NPC244890
0.755	Intermediate Similarity	NPC145722
0.755	Intermediate Similarity	NPC185680
0.755	Intermediate Similarity	NPC256776
0.7548	Intermediate Similarity	NPC470917
0.7548	Intermediate Similarity	NPC184641
0.7548	Intermediate Similarity	NPC230538
0.7548	Intermediate Similarity	NPC133934
0.7548	Intermediate Similarity	NPC103637
0.7548	Intermediate Similarity	NPC184684
0.7548	Intermediate Similarity	NPC36531
0.7548	Intermediate Similarity	NPC229172
0.7546	Intermediate Similarity	NPC475697
0.7517	Intermediate Similarity	NPC192687
0.7517	Intermediate Similarity	NPC126836
0.7517	Intermediate Similarity	NPC224157
0.75	Intermediate Similarity	NPC324962
0.75	Intermediate Similarity	NPC469630
0.7485	Intermediate Similarity	NPC474535
0.7483	Intermediate Similarity	NPC223953
0.7483	Intermediate Similarity	NPC32778
0.7452	Intermediate Similarity	NPC239254
0.7452	Intermediate Similarity	NPC73467
0.7452	Intermediate Similarity	NPC172171
0.7452	Intermediate Similarity	NPC87883
0.7452	Intermediate Similarity	NPC121661
0.7451	Intermediate Similarity	NPC205442
0.7451	Intermediate Similarity	NPC32189
0.7451	Intermediate Similarity	NPC202846
0.7451	Intermediate Similarity	NPC143139
0.745	Intermediate Similarity	NPC190144
0.7434	Intermediate Similarity	NPC125649
0.7434	Intermediate Similarity	NPC209199
0.7432	Intermediate Similarity	NPC471986
0.7432	Intermediate Similarity	NPC242032
0.7421	Intermediate Similarity	NPC137352
0.7421	Intermediate Similarity	NPC183083
0.7421	Intermediate Similarity	NPC295297
0.7417	Intermediate Similarity	NPC475856
0.7417	Intermediate Similarity	NPC6451
0.7417	Intermediate Similarity	NPC303011
0.7415	Intermediate Similarity	NPC105925
0.7405	Intermediate Similarity	NPC166506
0.7405	Intermediate Similarity	NPC197352
0.7405	Intermediate Similarity	NPC110763
0.7405	Intermediate Similarity	NPC475868
0.7405	Intermediate Similarity	NPC189239
0.7403	Intermediate Similarity	NPC865
0.7403	Intermediate Similarity	NPC266006
0.74	Intermediate Similarity	NPC258483
0.7386	Intermediate Similarity	NPC10314
0.7386	Intermediate Similarity	NPC241241
0.7386	Intermediate Similarity	NPC313081
0.7386	Intermediate Similarity	NPC294884
0.7386	Intermediate Similarity	NPC200557
0.7386	Intermediate Similarity	NPC108198
0.7386	Intermediate Similarity	NPC158142
0.7386	Intermediate Similarity	NPC69029
0.7383	Intermediate Similarity	NPC154866
0.7372	Intermediate Similarity	NPC118794
0.7368	Intermediate Similarity	NPC163560
0.7365	Intermediate Similarity	NPC76451
0.7358	Intermediate Similarity	NPC154971
0.7358	Intermediate Similarity	NPC474054
0.7358	Intermediate Similarity	NPC252286
0.7355	Intermediate Similarity	NPC230124
0.7355	Intermediate Similarity	NPC212942
0.7355	Intermediate Similarity	NPC184613
0.7355	Intermediate Similarity	NPC6300
0.7355	Intermediate Similarity	NPC79622
0.7355	Intermediate Similarity	NPC29868
0.7355	Intermediate Similarity	NPC114171
0.7351	Intermediate Similarity	NPC45715
0.7351	Intermediate Similarity	NPC12275
0.7351	Intermediate Similarity	NPC474356
0.7351	Intermediate Similarity	NPC232275
0.7338	Intermediate Similarity	NPC30632
0.7333	Intermediate Similarity	NPC474614
0.7329	Intermediate Similarity	NPC7398
0.732	Intermediate Similarity	NPC160697
0.732	Intermediate Similarity	NPC245386
0.7315	Intermediate Similarity	NPC202904
0.7315	Intermediate Similarity	NPC127587
0.7315	Intermediate Similarity	NPC74817
0.7315	Intermediate Similarity	NPC236791
0.7315	Intermediate Similarity	NPC169474
0.7315	Intermediate Similarity	NPC82679
0.7315	Intermediate Similarity	NPC159968
0.7315	Intermediate Similarity	NPC189248
0.7315	Intermediate Similarity	NPC324112
0.7315	Intermediate Similarity	NPC293054
0.7315	Intermediate Similarity	NPC282000
0.7315	Intermediate Similarity	NPC246620
0.7315	Intermediate Similarity	NPC266555
0.7315	Intermediate Similarity	NPC124452
0.7308	Intermediate Similarity	NPC12668
0.7308	Intermediate Similarity	NPC308768
0.7303	Intermediate Similarity	NPC161958
0.7303	Intermediate Similarity	NPC14224
0.729	Intermediate Similarity	NPC22902
0.729	Intermediate Similarity	NPC242715
0.729	Intermediate Similarity	NPC56329
0.7285	Intermediate Similarity	NPC311680
0.7285	Intermediate Similarity	NPC234488
0.7285	Intermediate Similarity	NPC51840
0.7285	Intermediate Similarity	NPC299221
0.7284	Intermediate Similarity	NPC470916
0.7279	Intermediate Similarity	NPC233526
0.7279	Intermediate Similarity	NPC282496
0.7278	Intermediate Similarity	NPC258083
0.7273	Intermediate Similarity	NPC111655
0.7273	Intermediate Similarity	NPC256262
0.7267	Intermediate Similarity	NPC325720
0.7267	Intermediate Similarity	NPC28765
0.7267	Intermediate Similarity	NPC316676
0.7267	Intermediate Similarity	NPC477879
0.726	Intermediate Similarity	NPC477886
0.7248	Intermediate Similarity	NPC28730
0.7248	Intermediate Similarity	NPC18924
0.7248	Intermediate Similarity	NPC78974
0.7248	Intermediate Similarity	NPC82299
0.7248	Intermediate Similarity	NPC134219
0.7248	Intermediate Similarity	NPC214406
0.7248	Intermediate Similarity	NPC103823
0.7248	Intermediate Similarity	NPC44748
0.7248	Intermediate Similarity	NPC223136
0.7244	Intermediate Similarity	NPC243759
0.7244	Intermediate Similarity	NPC132804
0.7244	Intermediate Similarity	NPC218131
0.7244	Intermediate Similarity	NPC275061
0.7244	Intermediate Similarity	NPC220344
0.7244	Intermediate Similarity	NPC243996
0.7244	Intermediate Similarity	NPC105847
0.7239	Intermediate Similarity	NPC224472
0.7237	Intermediate Similarity	NPC149337
0.7237	Intermediate Similarity	NPC471983
0.7237	Intermediate Similarity	NPC474017
0.7237	Intermediate Similarity	NPC15543
0.7226	Intermediate Similarity	NPC248727
0.7226	Intermediate Similarity	NPC270456
0.7226	Intermediate Similarity	NPC162659
0.7226	Intermediate Similarity	NPC173660
0.7226	Intermediate Similarity	NPC197166
0.7226	Intermediate Similarity	NPC265433
0.7222	Intermediate Similarity	NPC474393
0.7222	Intermediate Similarity	NPC474347
0.7219	Intermediate Similarity	NPC58164
0.7219	Intermediate Similarity	NPC10225
0.7219	Intermediate Similarity	NPC469963
0.7219	Intermediate Similarity	NPC85049
0.7219	Intermediate Similarity	NPC469951
0.7215	Intermediate Similarity	NPC175838
0.7208	Intermediate Similarity	NPC312155
0.72	Intermediate Similarity	NPC473221
0.72	Intermediate Similarity	NPC252131
0.7197	Intermediate Similarity	NPC109240
0.719	Intermediate Similarity	NPC127624
0.719	Intermediate Similarity	NPC175067
0.719	Intermediate Similarity	NPC204215
0.719	Intermediate Similarity	NPC300678
0.7188	Intermediate Similarity	NPC221318
0.7181	Intermediate Similarity	NPC475169
0.7181	Intermediate Similarity	NPC234400
0.7181	Intermediate Similarity	NPC193544
0.7181	Intermediate Similarity	NPC17943

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 NPC113862 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	472
0.1-0.2	1263
0.2-0.3	2947
0.3-0.4	2549
0.4-0.5	1204
0.5-0.6	634
0.6-0.7	80
0.7-0.8	1
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
0.7105	Intermediate Similarity	NPD3027	Phase 3
0.6882	Remote Similarity	NPD8095	Phase 1
0.6864	Remote Similarity	NPD4288	Approved
0.6863	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD3018	Phase 2
0.6818	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD5283	Phase 1
0.6752	Remote Similarity	NPD1613	Approved
0.6752	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD4010	Discontinued
0.6711	Remote Similarity	NPD2983	Phase 2
0.6711	Remote Similarity	NPD2982	Phase 2
0.6667	Remote Similarity	NPD4625	Phase 3
0.6647	Remote Similarity	NPD37	Approved
0.6645	Remote Similarity	NPD2981	Phase 2
0.6626	Remote Similarity	NPD6674	Discontinued
0.6603	Remote Similarity	NPD4908	Phase 1
0.6532	Remote Similarity	NPD4966	Approved
0.6532	Remote Similarity	NPD4965	Approved
0.6532	Remote Similarity	NPD4967	Phase 2
0.6519	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6494	Remote Similarity	NPD4749	Approved
0.6488	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD3705	Approved
0.6471	Remote Similarity	NPD1610	Phase 2
0.6471	Remote Similarity	NPD4005	Discontinued
0.6457	Remote Similarity	NPD6234	Discontinued
0.6441	Remote Similarity	NPD6232	Discontinued
0.6425	Remote Similarity	NPD7473	Discontinued
0.6402	Remote Similarity	NPD3540	Phase 1
0.64	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.64	Remote Similarity	NPD4055	Discovery
0.6387	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6384	Remote Similarity	NPD7199	Phase 2
0.6364	Remote Similarity	NPD4287	Approved
0.6347	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6341	Remote Similarity	NPD3539	Phase 1
0.6313	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6313	Remote Similarity	NPD6687	Approved
0.6313	Remote Similarity	NPD6688	Approved
0.6312	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.631	Remote Similarity	NPD7124	Phase 2
0.6294	Remote Similarity	NPD2184	Approved
0.6294	Remote Similarity	NPD2183	Approved
0.6291	Remote Similarity	NPD7340	Approved
0.6264	Remote Similarity	NPD1934	Approved
0.6264	Remote Similarity	NPD5844	Phase 1
0.6235	Remote Similarity	NPD4060	Phase 1
0.6235	Remote Similarity	NPD3620	Phase 2
0.6235	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6229	Remote Similarity	NPD1465	Phase 2
0.6229	Remote Similarity	NPD2801	Approved
0.6228	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6226	Remote Similarity	NPD2861	Phase 2
0.622	Remote Similarity	NPD6111	Discontinued
0.6211	Remote Similarity	NPD5111	Phase 2
0.6211	Remote Similarity	NPD5110	Phase 2
0.6211	Remote Similarity	NPD5109	Approved
0.6209	Remote Similarity	NPD1548	Phase 1
0.6209	Remote Similarity	NPD7228	Approved
0.6207	Remote Similarity	NPD5089	Approved
0.6207	Remote Similarity	NPD5090	Approved
0.62	Remote Similarity	NPD1398	Phase 1
0.619	Remote Similarity	NPD3892	Phase 2
0.6174	Remote Similarity	NPD228	Approved
0.6145	Remote Similarity	NPD6100	Approved
0.6145	Remote Similarity	NPD6099	Approved
0.6136	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6135	Remote Similarity	NPD2238	Phase 2
0.6111	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6102	Remote Similarity	NPD3817	Phase 2
0.6098	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6098	Remote Similarity	NPD5124	Phase 1
0.6082	Remote Similarity	NPD4357	Discontinued
0.6076	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6075	Remote Similarity	NPD7240	Approved
0.6071	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6067	Remote Similarity	NPD3882	Suspended
0.6067	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6059	Remote Similarity	NPD2219	Phase 1
0.6057	Remote Similarity	NPD4675	Approved
0.6057	Remote Similarity	NPD4678	Approved
0.6056	Remote Similarity	NPD5494	Approved
0.6047	Remote Similarity	NPD2533	Approved
0.6047	Remote Similarity	NPD2532	Approved
0.6047	Remote Similarity	NPD2534	Approved
0.6043	Remote Similarity	NPD7549	Discontinued
0.604	Remote Similarity	NPD3022	Approved
0.604	Remote Similarity	NPD3021	Approved
0.604	Remote Similarity	NPD4750	Phase 3
0.6039	Remote Similarity	NPD5536	Phase 2
0.6038	Remote Similarity	NPD6696	Suspended
0.6036	Remote Similarity	NPD5177	Phase 3
0.6013	Remote Similarity	NPD2232	Approved
0.6013	Remote Similarity	NPD2233	Approved
0.6013	Remote Similarity	NPD2230	Approved
0.6012	Remote Similarity	NPD7985	Registered
0.6012	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.6011	Remote Similarity	NPD6374	Clinical (unspecified phase)
0.6011	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6011	Remote Similarity	NPD6166	Phase 2
0.6011	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6055	Clinical (unspecified phase)
0.6	Remote Similarity	NPD3657	Discovery
0.5989	Remote Similarity	NPD7229	Phase 3
0.5988	Remote Similarity	NPD1511	Approved
0.5977	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.5965	Remote Similarity	NPD2677	Approved
0.5964	Remote Similarity	NPD6651	Approved
0.5964	Remote Similarity	NPD4097	Suspended
0.5963	Remote Similarity	NPD4624	Approved
0.5955	Remote Similarity	NPD7819	Suspended
0.5955	Remote Similarity	NPD4585	Approved
0.5943	Remote Similarity	NPD1653	Approved
0.5938	Remote Similarity	NPD1283	Approved
0.5935	Remote Similarity	NPD7644	Approved
0.5934	Remote Similarity	NPD6959	Discontinued
0.5924	Remote Similarity	NPD4626	Approved
0.5922	Remote Similarity	NPD2296	Approved
0.592	Remote Similarity	NPD1512	Approved
0.5917	Remote Similarity	NPD1375	Discontinued
0.5917	Remote Similarity	NPD5763	Approved
0.5917	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.5917	Remote Similarity	NPD5762	Approved
0.5915	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD7261	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD709	Approved
0.5909	Remote Similarity	NPD6671	Approved
0.5906	Remote Similarity	NPD3750	Approved
0.5906	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.5902	Remote Similarity	NPD3787	Discontinued
0.5896	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.5895	Remote Similarity	NPD8053	Approved
0.5895	Remote Similarity	NPD8054	Approved
0.5893	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.5893	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD7074	Phase 3
0.5875	Remote Similarity	NPD1669	Approved
0.587	Remote Similarity	NPD3926	Phase 2
0.5862	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.586	Remote Similarity	NPD8099	Discontinued
0.586	Remote Similarity	NPD3818	Discontinued
0.586	Remote Similarity	NPD8251	Approved
0.586	Remote Similarity	NPD8252	Approved
0.586	Remote Similarity	NPD1651	Approved
0.5854	Remote Similarity	NPD7095	Approved
0.5849	Remote Similarity	NPD422	Phase 1
0.5848	Remote Similarity	NPD4236	Phase 3
0.5848	Remote Similarity	NPD4237	Approved
0.5848	Remote Similarity	NPD3060	Approved
0.5843	Remote Similarity	NPD1240	Approved
0.5843	Remote Similarity	NPD1558	Phase 1
0.5842	Remote Similarity	NPD3337	Discontinued
0.5839	Remote Similarity	NPD8651	Approved
0.5839	Remote Similarity	NPD2922	Phase 1
0.5833	Remote Similarity	NPD6895	Approved
0.5833	Remote Similarity	NPD6896	Approved
0.5833	Remote Similarity	NPD2560	Approved
0.5833	Remote Similarity	NPD2563	Approved
0.5829	Remote Similarity	NPD8156	Discontinued
0.5829	Remote Similarity	NPD7054	Approved
0.5829	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.5823	Remote Similarity	NPD2667	Approved
0.5823	Remote Similarity	NPD2668	Approved
0.5817	Remote Similarity	NPD7635	Approved
0.5814	Remote Similarity	NPD4110	Phase 3
0.5814	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.5814	Remote Similarity	NPD7982	Clinical (unspecified phase)
0.5814	Remote Similarity	NPD6331	Phase 2
0.5814	Remote Similarity	NPD7466	Approved
0.5812	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.5811	Remote Similarity	NPD9244	Approved
0.5808	Remote Similarity	NPD5735	Approved
0.5808	Remote Similarity	NPD6355	Discontinued
0.5806	Remote Similarity	NPD7157	Approved
0.5801	Remote Similarity	NPD6788	Approved
0.5799	Remote Similarity	NPD4108	Discontinued
0.5799	Remote Similarity	NPD1510	Phase 2
0.5799	Remote Similarity	NPD3748	Approved
0.5798	Remote Similarity	NPD7472	Approved
0.5789	Remote Similarity	NPD4664	Clinical (unspecified phase)
0.5787	Remote Similarity	NPD2804	Phase 1
0.5787	Remote Similarity	NPD4380	Phase 2
0.5782	Remote Similarity	NPD940	Approved
0.5782	Remote Similarity	NPD846	Approved
0.578	Remote Similarity	NPD5241	Discontinued
0.578	Remote Similarity	NPD5084	Clinical (unspecified phase)
0.5774	Remote Similarity	NPD1607	Approved
0.5771	Remote Similarity	NPD4123	Phase 3
0.5771	Remote Similarity	NPD4584	Approved
0.5771	Remote Similarity	NPD7447	Phase 1
0.5765	Remote Similarity	NPD2438	Suspended
0.5765	Remote Similarity	NPD2935	Discontinued
0.5762	Remote Similarity	NPD2684	Approved
0.5759	Remote Similarity	NPD5691	Approved
0.5759	Remote Similarity	NPD1357	Approved
0.5756	Remote Similarity	NPD2800	Approved
0.5756	Remote Similarity	NPD1652	Phase 2
0.575	Remote Similarity	NPD1611	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