NPASS Compound

Structure

CID183083 OpenBabel06191715562D 36 38 0 0 1 0 0 0 0 0999 V2000 -2.1417 -4.4120 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6215 -2.6215 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1148 3.9891 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9020 3.6970 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1012 0.8310 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5078 0.8310 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4370 -1.3750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2703 -2.2703 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7994 -1.0709 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4863 -3.7566 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4155 2.4774 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3107 1.3107 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7173 1.3107 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8221 2.4774 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7262 -2.8614 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2399 3.1328 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4155 1.5506 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8221 1.5506 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5506 0.4155 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9572 0.4155 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2399 0.8952 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1667 0.8952 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3018 -0.2399 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8952 -0.2399 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4066 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 -1.0709 -2.2060 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1667 3.1328 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.1756 -2.4459 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0457 4.0517 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4459 0.1756 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8525 0.1756 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5417 -1.1351 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3750 -2.0304 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0959 -1.3107 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3107 -1.3107 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 10 1 0 0 0 0 2 15 1 0 0 0 0 3 16 1 0 0 0 0 5 31 1 0 0 0 0 6 32 1 0 0 0 0 7 33 1 0 0 0 0 8 34 1 0 0 0 0 9 35 1 0 0 0 0 10 15 2 0 0 0 0 11 16 1 0 0 0 0 11 17 1 0 0 0 0 12 17 2 0 0 0 0 12 19 1 0 0 0 0 13 18 2 0 0 0 0 13 20 1 0 0 0 0 14 18 1 0 0 0 0 14 28 1 0 0 0 0 15 27 1 0 0 0 0 16 28 1 1 0 0 0 17 21 1 0 0 0 0 18 22 1 0 0 0 0 19 24 2 0 0 0 0 19 31 1 0 0 0 0 20 23 2 0 0 0 0 20 32 1 0 0 0 0 21 22 1 0 0 0 0 21 26 2 0 0 0 0 22 25 2 0 0 0 0 23 25 1 0 0 0 0 23 33 1 0 0 0 0 24 26 1 0 0 0 0 24 34 1 0 0 0 0 25 35 1 0 0 0 0 26 36 1 0 0 0 0 27 29 2 0 0 0 0 27 36 1 0 0 0 0 28 4 1 1 0 0 0 28 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	500.24
Volume:	516.405
LogP:	3.906
LogD:	3.484
LogS:	-4.925
# Rotatable Bonds:	8
TPSA:	92.68
# H-Bond Aceptor:	8
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.331
Synthetic Accessibility Score:	3.785
Fsp3:	0.464
Lipinski Rule-of-5:	Accepted
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:	-4.889
MDCK Permeability:	2.3034413970890455e-05
Pgp-inhibitor:	0.993
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.027
20% Bioavailability (F20%):	0.024
30% Bioavailability (F30%):	0.182

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.039
Plasma Protein Binding (PPB):	72.45011138916016%
Volume Distribution (VD):	0.724
Pgp-substrate:	30.503765106201172%

ADMET: Metabolism

CYP1A2-inhibitor:	0.091
CYP1A2-substrate:	0.98
CYP2C19-inhibitor:	0.542
CYP2C19-substrate:	0.919
CYP2C9-inhibitor:	0.48
CYP2C9-substrate:	0.893
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.876
CYP3A4-inhibitor:	0.838
CYP3A4-substrate:	0.799

ADMET: Excretion

Clearance (CL):	6.495
Half-life (T1/2):	0.181

ADMET: Toxicity

hERG Blockers:	0.035
Human Hepatotoxicity (H-HT):	0.043
Drug-inuced Liver Injury (DILI):	0.079
AMES Toxicity:	0.019
Rat Oral Acute Toxicity:	0.391
Maximum Recommended Daily Dose:	0.16
Skin Sensitization:	0.24
Carcinogencity:	0.021
Eye Corrosion:	0.003
Eye Irritation:	0.069
Respiratory Toxicity:	0.46

Download Data

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

Natural Product: NPC183083

Natural Product ID:	NPC183083
*Common Name:**	Tigloylgomisin H
IUPAC Name:	n.a.
Synonyms:	Tigloylgomisin H
Standard InCHIKey:	ZSAUXCVJDYCLRS-QEEHVONISA-N
Standard InCHI:	InChI=1S/C28H36O8/c1-10-15(2)27(29)36-26-21-17(12-19(31-5)24(26)34-8)11-16(3)28(4,30)14-18-13-20(32-6)23(33-7)25(35-9)22(18)21/h10,12-13,16,30H,11,14H2,1-9H3/b15-10+/t16-,28-/m0/s1
SMILES:	C/C=C(/C(=O)Oc1c(OC)c(OC)cc2c1c1c(cc(c(c1OC)OC)OC)C[C@]([C@H](C2)C)(C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1093179
PubChem CID:	5318766
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]
NPO8187	Schisandra chinensis	Species	Schisandraceae	Eukaryota	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
IC50	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	124900.0	nM	PMID[503960]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	44300.0	nM	PMID[503960]

☑ 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 NPC183083 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	348
0.1-0.2	1457
0.2-0.3	3687
0.3-0.4	9433
0.4-0.5	9310
0.5-0.6	3482
0.6-0.7	6932
0.7-0.8	7386
0.8-0.85	549
0.85-0.9	82
0.9-0.95	25
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC137352
0.965	High Similarity	NPC477381
0.9583	High Similarity	NPC477379
0.9577	High Similarity	NPC295297
0.9452	High Similarity	NPC149735
0.9379	High Similarity	NPC470916
0.9375	High Similarity	NPC477879
0.931	High Similarity	NPC474393
0.931	High Similarity	NPC474347
0.9267	High Similarity	NPC328122
0.9262	High Similarity	NPC473323
0.9189	High Similarity	NPC53669
0.9189	High Similarity	NPC217708
0.9189	High Similarity	NPC77237
0.9189	High Similarity	NPC308739
0.9189	High Similarity	NPC297271
0.9189	High Similarity	NPC16791
0.9189	High Similarity	NPC126405
0.9078	High Similarity	NPC865
0.906	High Similarity	NPC24562
0.9054	High Similarity	NPC224472
0.9	High Similarity	NPC473736
0.9	High Similarity	NPC473425
0.9	High Similarity	NPC198461
0.8993	High Similarity	NPC102256
0.898	High Similarity	NPC327352
0.898	High Similarity	NPC198129
0.898	High Similarity	NPC477375
0.898	High Similarity	NPC252281
0.8973	High Similarity	NPC474054
0.8966	High Similarity	NPC87883
0.8961	High Similarity	NPC249070
0.8947	High Similarity	NPC475592
0.894	High Similarity	NPC476065
0.8933	High Similarity	NPC475141
0.8919	High Similarity	NPC477376
0.8919	High Similarity	NPC322426
0.8919	High Similarity	NPC477374
0.8882	High Similarity	NPC29727
0.8874	High Similarity	NPC312763
0.8859	High Similarity	NPC316989
0.8792	High Similarity	NPC85141
0.8776	High Similarity	NPC327651
0.8776	High Similarity	NPC318286
0.8742	High Similarity	NPC471154
0.8725	High Similarity	NPC325720
0.8725	High Similarity	NPC316676
0.8718	High Similarity	NPC42797
0.8716	High Similarity	NPC321696
0.8716	High Similarity	NPC321958
0.871	High Similarity	NPC63061
0.8707	High Similarity	NPC326144
0.8705	High Similarity	NPC207702
0.8705	High Similarity	NPC149008
0.8705	High Similarity	NPC283114
0.8684	High Similarity	NPC474606
0.8684	High Similarity	NPC477377
0.8675	High Similarity	NPC475756
0.8671	High Similarity	NPC240279
0.8671	High Similarity	NPC180602
0.8671	High Similarity	NPC55239
0.8671	High Similarity	NPC214853
0.8662	High Similarity	NPC291977
0.8658	High Similarity	NPC178129
0.8652	High Similarity	NPC184928
0.8652	High Similarity	NPC141493
0.8645	High Similarity	NPC230531
0.8645	High Similarity	NPC215400
0.8639	High Similarity	NPC218510
0.8639	High Similarity	NPC76415
0.8621	High Similarity	NPC290714
0.8621	High Similarity	NPC53722
0.8621	High Similarity	NPC471183
0.8621	High Similarity	NPC201404
0.8618	High Similarity	NPC475229
0.8618	High Similarity	NPC477378
0.8611	High Similarity	NPC286843
0.8609	High Similarity	NPC473989
0.8601	High Similarity	NPC188378
0.8601	High Similarity	NPC206737
0.8601	High Similarity	NPC469659
0.8601	High Similarity	NPC289258
0.8601	High Similarity	NPC276026
0.8601	High Similarity	NPC56764
0.8601	High Similarity	NPC555
0.8601	High Similarity	NPC7515
0.8599	High Similarity	NPC473445
0.8592	High Similarity	NPC245120
0.8591	High Similarity	NPC205361
0.8571	High Similarity	NPC238834
0.8571	High Similarity	NPC474651
0.8571	High Similarity	NPC474623
0.8553	High Similarity	NPC83049
0.8553	High Similarity	NPC118162
0.8553	High Similarity	NPC320471
0.8552	High Similarity	NPC105493
0.8542	High Similarity	NPC224941
0.8542	High Similarity	NPC234865
0.8542	High Similarity	NPC311430
0.8533	High Similarity	NPC15577
0.8523	High Similarity	NPC125617
0.8516	High Similarity	NPC477380
0.8514	High Similarity	NPC7439
0.8514	High Similarity	NPC110067
0.8514	High Similarity	NPC6568
0.8514	High Similarity	NPC91492
0.8514	High Similarity	NPC256555
0.8514	High Similarity	NPC34245
0.8506	High Similarity	NPC348849
0.8506	High Similarity	NPC178195
0.8503	High Similarity	NPC300611
0.85	High Similarity	NPC194841
0.8493	Intermediate Similarity	NPC164148
0.8493	Intermediate Similarity	NPC43500
0.8483	Intermediate Similarity	NPC471719
0.8483	Intermediate Similarity	NPC133025
0.8477	Intermediate Similarity	NPC476348
0.8477	Intermediate Similarity	NPC93924
0.8477	Intermediate Similarity	NPC187398
0.8472	Intermediate Similarity	NPC474600
0.8472	Intermediate Similarity	NPC309744
0.8472	Intermediate Similarity	NPC111635
0.8462	Intermediate Similarity	NPC477885
0.8462	Intermediate Similarity	NPC319969
0.8462	Intermediate Similarity	NPC5423
0.8456	Intermediate Similarity	NPC18211
0.8456	Intermediate Similarity	NPC36732
0.8456	Intermediate Similarity	NPC143092
0.8451	Intermediate Similarity	NPC476399
0.8451	Intermediate Similarity	NPC307042
0.8451	Intermediate Similarity	NPC79184
0.8451	Intermediate Similarity	NPC19242
0.8425	Intermediate Similarity	NPC156948
0.8425	Intermediate Similarity	NPC46277
0.8425	Intermediate Similarity	NPC474886
0.8425	Intermediate Similarity	NPC86605
0.8425	Intermediate Similarity	NPC301765
0.8425	Intermediate Similarity	NPC3072
0.8421	Intermediate Similarity	NPC176903
0.8421	Intermediate Similarity	NPC113790
0.8421	Intermediate Similarity	NPC30688
0.8411	Intermediate Similarity	NPC275125
0.8411	Intermediate Similarity	NPC97937
0.8411	Intermediate Similarity	NPC476347
0.8411	Intermediate Similarity	NPC170239
0.8408	Intermediate Similarity	NPC37502
0.8408	Intermediate Similarity	NPC267627
0.8408	Intermediate Similarity	NPC40702
0.8403	Intermediate Similarity	NPC241341
0.8403	Intermediate Similarity	NPC36437
0.8403	Intermediate Similarity	NPC233018
0.84	Intermediate Similarity	NPC86069
0.8397	Intermediate Similarity	NPC54928
0.8397	Intermediate Similarity	NPC469474
0.8395	Intermediate Similarity	NPC477883
0.8389	Intermediate Similarity	NPC230157
0.8389	Intermediate Similarity	NPC469630
0.8389	Intermediate Similarity	NPC324962
0.8389	Intermediate Similarity	NPC138212
0.8385	Intermediate Similarity	NPC79322
0.8378	Intermediate Similarity	NPC472523
0.8377	Intermediate Similarity	NPC272566
0.8367	Intermediate Similarity	NPC270256
0.8366	Intermediate Similarity	NPC294522
0.8366	Intermediate Similarity	NPC21184
0.8366	Intermediate Similarity	NPC120426
0.8366	Intermediate Similarity	NPC205727
0.8365	Intermediate Similarity	NPC469512
0.8355	Intermediate Similarity	NPC252402
0.8355	Intermediate Similarity	NPC102934
0.8355	Intermediate Similarity	NPC139839
0.8355	Intermediate Similarity	NPC48366
0.8345	Intermediate Similarity	NPC145722
0.8345	Intermediate Similarity	NPC92830
0.8345	Intermediate Similarity	NPC256776
0.8345	Intermediate Similarity	NPC185680
0.8344	Intermediate Similarity	NPC125495
0.8344	Intermediate Similarity	NPC247713
0.8344	Intermediate Similarity	NPC40222
0.8344	Intermediate Similarity	NPC475872
0.8344	Intermediate Similarity	NPC287275
0.8344	Intermediate Similarity	NPC268515
0.8333	Intermediate Similarity	NPC88557
0.8333	Intermediate Similarity	NPC471824
0.8333	Intermediate Similarity	NPC471763
0.8333	Intermediate Similarity	NPC117154
0.8333	Intermediate Similarity	NPC137669
0.8323	Intermediate Similarity	NPC476154
0.8322	Intermediate Similarity	NPC469564
0.8322	Intermediate Similarity	NPC229172
0.8322	Intermediate Similarity	NPC103637
0.8322	Intermediate Similarity	NPC133934
0.8322	Intermediate Similarity	NPC184684
0.8322	Intermediate Similarity	NPC184641
0.8322	Intermediate Similarity	NPC36531
0.8322	Intermediate Similarity	NPC244799
0.8322	Intermediate Similarity	NPC474617
0.8322	Intermediate Similarity	NPC240722
0.8322	Intermediate Similarity	NPC230538
0.8313	Intermediate Similarity	NPC300984

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 NPC183083 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	301
0.1-0.2	938
0.2-0.3	1782
0.3-0.4	2714
0.4-0.5	1740
0.5-0.6	965
0.6-0.7	562
0.7-0.8	145
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8153	Intermediate Similarity	NPD1465	Phase 2
0.811	Intermediate Similarity	NPD5844	Phase 1
0.7988	Intermediate Similarity	NPD7473	Discontinued
0.7975	Intermediate Similarity	NPD37	Approved
0.7963	Intermediate Similarity	NPD7199	Phase 2
0.7937	Intermediate Similarity	NPD4966	Approved
0.7937	Intermediate Similarity	NPD4967	Phase 2
0.7937	Intermediate Similarity	NPD4965	Approved
0.7937	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7935	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7925	Intermediate Similarity	NPD7819	Suspended
0.7914	Intermediate Similarity	NPD6232	Discontinued
0.7875	Intermediate Similarity	NPD3817	Phase 2
0.7866	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7843	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.784	Intermediate Similarity	NPD6234	Discontinued
0.7834	Intermediate Similarity	NPD1653	Approved
0.7823	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7808	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7755	Intermediate Similarity	NPD3027	Phase 3
0.7727	Intermediate Similarity	NPD3750	Approved
0.7718	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7718	Intermediate Similarity	NPD4060	Phase 1
0.7718	Intermediate Similarity	NPD1613	Approved
0.7706	Intermediate Similarity	NPD7549	Discontinued
0.7692	Intermediate Similarity	NPD422	Phase 1
0.764	Intermediate Similarity	NPD1934	Approved
0.7636	Intermediate Similarity	NPD8127	Discontinued
0.7635	Intermediate Similarity	NPD4625	Phase 3
0.7632	Intermediate Similarity	NPD3748	Approved
0.7619	Intermediate Similarity	NPD7228	Approved
0.7619	Intermediate Similarity	NPD3018	Phase 2
0.7597	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD2801	Approved
0.7568	Intermediate Similarity	NPD4908	Phase 1
0.755	Intermediate Similarity	NPD5124	Phase 1
0.755	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD7095	Approved
0.75	Intermediate Similarity	NPD3882	Suspended
0.7485	Intermediate Similarity	NPD7229	Phase 3
0.7485	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD2797	Approved
0.747	Intermediate Similarity	NPD5494	Approved
0.7468	Intermediate Similarity	NPD6100	Approved
0.7468	Intermediate Similarity	NPD6799	Approved
0.7468	Intermediate Similarity	NPD6099	Approved
0.7467	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7466	Intermediate Similarity	NPD4749	Approved
0.7466	Intermediate Similarity	NPD2983	Phase 2
0.7466	Intermediate Similarity	NPD2982	Phase 2
0.7455	Intermediate Similarity	NPD7075	Discontinued
0.7448	Intermediate Similarity	NPD1610	Phase 2
0.7442	Intermediate Similarity	NPD7240	Approved
0.7436	Intermediate Similarity	NPD1652	Phase 2
0.7436	Intermediate Similarity	NPD6674	Discontinued
0.7434	Intermediate Similarity	NPD6355	Discontinued
0.7434	Intermediate Similarity	NPD447	Suspended
0.7429	Intermediate Similarity	NPD5283	Phase 1
0.7427	Intermediate Similarity	NPD7074	Phase 3
0.7419	Intermediate Similarity	NPD5763	Approved
0.7419	Intermediate Similarity	NPD5762	Approved
0.7412	Intermediate Similarity	NPD3818	Discontinued
0.741	Intermediate Similarity	NPD919	Approved
0.7407	Intermediate Similarity	NPD6599	Discontinued
0.7397	Intermediate Similarity	NPD2981	Phase 2
0.7396	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD6166	Phase 2
0.7394	Intermediate Similarity	NPD7768	Phase 2
0.7384	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD7054	Approved
0.7358	Intermediate Similarity	NPD1511	Approved
0.7358	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD3268	Approved
0.7349	Intermediate Similarity	NPD3749	Approved
0.7347	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7343	Intermediate Similarity	NPD5536	Phase 2
0.7337	Intermediate Similarity	NPD3926	Phase 2
0.7329	Intermediate Similarity	NPD3705	Approved
0.7329	Intermediate Similarity	NPD1611	Approved
0.7326	Intermediate Similarity	NPD7472	Approved
0.731	Intermediate Similarity	NPD4626	Approved
0.7308	Intermediate Similarity	NPD7266	Discontinued
0.7279	Intermediate Similarity	NPD1608	Approved
0.7278	Intermediate Similarity	NPD4628	Phase 3
0.7278	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD4110	Phase 3
0.7273	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD1512	Approved
0.7256	Intermediate Similarity	NPD5089	Approved
0.7256	Intermediate Similarity	NPD5090	Approved
0.7256	Intermediate Similarity	NPD7411	Suspended
0.725	Intermediate Similarity	NPD4357	Discontinued
0.7246	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD2935	Discontinued
0.7241	Intermediate Similarity	NPD5691	Approved
0.7239	Intermediate Similarity	NPD3226	Approved
0.7229	Intermediate Similarity	NPD5402	Approved
0.7226	Intermediate Similarity	NPD7097	Phase 1
0.7219	Intermediate Similarity	NPD6832	Phase 2
0.7219	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD6959	Discontinued
0.7212	Intermediate Similarity	NPD6801	Discontinued
0.7208	Intermediate Similarity	NPD230	Phase 1
0.7205	Intermediate Similarity	NPD2532	Approved
0.7205	Intermediate Similarity	NPD2533	Approved
0.7205	Intermediate Similarity	NPD2534	Approved
0.7205	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD7808	Phase 3
0.72	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD6842	Approved
0.7191	Intermediate Similarity	NPD6841	Approved
0.7191	Intermediate Similarity	NPD6843	Phase 3
0.7181	Intermediate Similarity	NPD1283	Approved
0.7181	Intermediate Similarity	NPD3225	Approved
0.7179	Intermediate Similarity	NPD2799	Discontinued
0.7172	Intermediate Similarity	NPD1548	Phase 1
0.7152	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD2861	Phase 2
0.7151	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4140	Approved
0.7143	Intermediate Similarity	NPD3496	Discontinued
0.7143	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7251	Discontinued
0.7143	Intermediate Similarity	NPD6559	Discontinued
0.7135	Intermediate Similarity	NPD5242	Approved
0.7134	Intermediate Similarity	NPD2438	Suspended
0.7134	Intermediate Similarity	NPD1551	Phase 2
0.7134	Intermediate Similarity	NPD2796	Approved
0.7134	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD3267	Approved
0.7133	Intermediate Similarity	NPD3266	Approved
0.7126	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD5353	Approved
0.7125	Intermediate Similarity	NPD6190	Approved
0.7124	Intermediate Similarity	NPD1296	Phase 2
0.7124	Intermediate Similarity	NPD6798	Discontinued
0.7124	Intermediate Similarity	NPD7985	Registered
0.7117	Intermediate Similarity	NPD5403	Approved
0.7113	Intermediate Similarity	NPD5535	Approved
0.711	Intermediate Similarity	NPD3751	Discontinued
0.7107	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD1243	Approved
0.7107	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD5401	Approved
0.7099	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD1933	Approved
0.7093	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD4380	Phase 2
0.7089	Intermediate Similarity	NPD2346	Discontinued
0.7089	Intermediate Similarity	NPD3540	Phase 1
0.7086	Intermediate Similarity	NPD6797	Phase 2
0.7081	Intermediate Similarity	NPD6666	Approved
0.7081	Intermediate Similarity	NPD6667	Approved
0.7076	Intermediate Similarity	NPD3787	Discontinued
0.7075	Intermediate Similarity	NPD17	Approved
0.707	Intermediate Similarity	NPD4308	Phase 3
0.7066	Intermediate Similarity	NPD8455	Phase 2
0.7063	Intermediate Similarity	NPD3892	Phase 2
0.7055	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD6273	Approved
0.7044	Intermediate Similarity	NPD1549	Phase 2
0.7041	Intermediate Similarity	NPD4055	Discovery
0.7039	Intermediate Similarity	NPD8434	Phase 2
0.7037	Intermediate Similarity	NPD7837	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD1240	Approved
0.7032	Intermediate Similarity	NPD2979	Phase 3
0.703	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD4005	Discontinued
0.7025	Intermediate Similarity	NPD6032	Approved
0.7025	Intermediate Similarity	NPD3539	Phase 1
0.7024	Intermediate Similarity	NPD4288	Approved
0.7024	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD1247	Approved
0.7012	Intermediate Similarity	NPD920	Approved
0.7007	Intermediate Similarity	NPD5585	Approved
0.7	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD7644	Approved
0.6981	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.698	Remote Similarity	NPD1281	Approved
0.6975	Remote Similarity	NPD7124	Phase 2
0.697	Remote Similarity	NPD3687	Approved
0.697	Remote Similarity	NPD3686	Approved
0.6968	Remote Similarity	NPD8032	Phase 2
0.6968	Remote Similarity	NPD6233	Phase 2
0.6966	Remote Similarity	NPD7157	Approved
0.6966	Remote Similarity	NPD6671	Approved
0.6964	Remote Similarity	NPD4585	Approved
0.6962	Remote Similarity	NPD1510	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