NPASS Compound

Structure

CID85141 OpenBabel06191715422D 35 39 0 0 1 0 0 0 0 0999 V2000 -0.3271 6.8296 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7122 4.7284 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9121 5.1878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2328 5.1878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6952 -1.1703 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4497 -1.1703 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0817 6.2506 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2207 3.6364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1395 2.4390 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0054 2.4390 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0844 0.1488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9395 0.1488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9576 5.3075 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5481 4.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5968 4.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.2207 2.6852 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9242 2.6852 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3857 1.5202 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2408 1.5202 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5481 2.0125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5968 2.0125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9242 3.6364 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.7131 0.8475 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4318 0.8475 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7943 1.0937 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3507 1.0937 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0787 4.9435 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6759 5.5225 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4490 -0.2515 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6959 -0.2515 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2332 1.0883 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0883 1.0883 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1449 -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 0.0454 4.0004 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 7 1 0 0 0 0 2 13 1 0 0 0 0 5 29 1 0 0 0 0 6 30 1 0 0 0 0 7 13 2 0 0 0 0 8 14 1 0 0 0 0 8 16 1 0 0 0 0 9 16 2 0 0 0 0 9 18 1 0 0 0 0 10 17 2 0 0 0 0 10 19 1 0 0 0 0 11 31 1 0 0 0 0 11 33 1 0 0 0 0 12 32 1 0 0 0 0 12 34 1 0 0 0 0 13 27 1 0 0 0 0 14 3 1 1 0 0 0 14 15 1 0 0 0 0 15 4 1 1 0 0 0 15 22 1 0 0 0 0 16 20 1 0 0 0 0 17 21 1 0 0 0 0 17 22 1 0 0 0 0 18 23 2 0 0 0 0 18 31 1 0 0 0 0 19 24 2 0 0 0 0 19 32 1 0 0 0 0 20 21 1 0 0 0 0 20 25 2 0 0 0 0 21 26 2 0 0 0 0 22 35 1 6 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 29 1 0 0 0 0 26 30 1 0 0 0 0 27 28 2 0 0 0 0 27 35 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	482.19
Volume:	481.996
LogP:	4.705
LogD:	4.202
LogS:	-6.149
# Rotatable Bonds:	5
TPSA:	81.68
# H-Bond Aceptor:	8
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.434
Synthetic Accessibility Score:	4.205
Fsp3:	0.444
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.828
MDCK Permeability:	3.0168366720317863e-05
Pgp-inhibitor:	0.993
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.027

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.028
Plasma Protein Binding (PPB):	89.7994613647461%
Volume Distribution (VD):	1.064
Pgp-substrate:	5.073634624481201%

ADMET: Metabolism

CYP1A2-inhibitor:	0.237
CYP1A2-substrate:	0.816
CYP2C19-inhibitor:	0.985
CYP2C19-substrate:	0.837
CYP2C9-inhibitor:	0.957
CYP2C9-substrate:	0.916
CYP2D6-inhibitor:	0.579
CYP2D6-substrate:	0.683
CYP3A4-inhibitor:	0.971
CYP3A4-substrate:	0.759

ADMET: Excretion

Clearance (CL):	10.188
Half-life (T1/2):	0.082

ADMET: Toxicity

hERG Blockers:	0.054
Human Hepatotoxicity (H-HT):	0.151
Drug-inuced Liver Injury (DILI):	0.798
AMES Toxicity:	0.073
Rat Oral Acute Toxicity:	0.023
Maximum Recommended Daily Dose:	0.314
Skin Sensitization:	0.316
Carcinogencity:	0.842
Eye Corrosion:	0.003
Eye Irritation:	0.278
Respiratory Toxicity:	0.767

Download Data

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

Natural Product: NPC85141

Natural Product ID:	NPC85141
*Common Name:**	Angeloylgomisin R
IUPAC Name:	n.a.
Synonyms:	Angeloylgomisin R
Standard InCHIKey:	RKXVNKMVDVIIQH-KNXRCIGESA-N
Standard InCHI:	InChI=1S/C27H30O8/c1-7-13(2)27(28)35-22-15(4)14(3)8-16-9-18-23(33-11-31-18)25(29-5)20(16)21-17(22)10-19-24(26(21)30-6)34-12-32-19/h7,9-10,14-15,22H,8,11-12H2,1-6H3/b13-7-/t14-,15-,22+/m0/s1
SMILES:	C/C=C(C(=O)O[C@@H]1[C@@H](C)[C@@H](C)Cc2c(c3c1cc1OCOc1c3OC)c(OC)c1c(c2)OCO1)/C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL489960
PubChem CID:	44593602
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
NPO14102	Kadsura interior	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12350139]
NPO14102	Kadsura interior	Species	Schisandraceae	Eukaryota	n.a.	stem	n.a.	PMID[8946749]
NPO14102	Kadsura interior	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14102	Kadsura interior	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14102	Kadsura interior	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	1
Others	5

Activity Type	# Activity
Cell Line	1
Organism	1
Others	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT80	Cell Line	Raji	Homo sapiens	Activity	=	60.0	%	PMID[535850]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	IC50	=	34.0	ug.mL-1	PMID[535849]
NPT2	Others	Unspecified		Activity	=	10.6	%	PMID[535850]
NPT2	Others	Unspecified		Activity	=	55.6	%	PMID[535850]
NPT2	Others	Unspecified		Activity	=	79.0	%	PMID[535850]
NPT2	Others	Unspecified		Activity	=	100.0	%	PMID[535850]

☑ 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 NPC85141 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	380
0.1-0.2	1600
0.2-0.3	3983
0.3-0.4	9701
0.4-0.5	8995
0.5-0.6	4141
0.6-0.7	8829
0.7-0.8	4575
0.8-0.85	307
0.85-0.9	127
0.9-0.95	48
0.95-1	11

Similarity Score	Similarity Level	Natural Product ID
0.9789	High Similarity	NPC477375
0.9789	High Similarity	NPC198129
0.9789	High Similarity	NPC252281
0.9789	High Similarity	NPC327352
0.972	High Similarity	NPC477374
0.972	High Similarity	NPC477376
0.972	High Similarity	NPC322426
0.9658	High Similarity	NPC178195
0.9658	High Similarity	NPC312763
0.9658	High Similarity	NPC348849
0.9658	High Similarity	NPC198461
0.9653	High Similarity	NPC316989
0.9577	High Similarity	NPC327651
0.9577	High Similarity	NPC318286
0.9574	High Similarity	NPC76415
0.9574	High Similarity	NPC218510
0.951	High Similarity	NPC321696
0.951	High Similarity	NPC321958
0.9507	High Similarity	NPC326144
0.9456	High Similarity	NPC308739
0.9456	High Similarity	NPC126405
0.9456	High Similarity	NPC24562
0.9456	High Similarity	NPC297271
0.9456	High Similarity	NPC217708
0.9456	High Similarity	NPC53669
0.9456	High Similarity	NPC16791
0.9456	High Similarity	NPC477377
0.9456	High Similarity	NPC77237
0.9452	High Similarity	NPC303519
0.9388	High Similarity	NPC477378
0.9388	High Similarity	NPC475229
0.9384	High Similarity	NPC473989
0.9329	High Similarity	NPC476065
0.932	High Similarity	NPC224472
0.9276	High Similarity	NPC191352
0.9276	High Similarity	NPC258322
0.9267	High Similarity	NPC473323
0.9267	High Similarity	NPC477380
0.9247	High Similarity	NPC316676
0.9247	High Similarity	NPC325720
0.9205	High Similarity	NPC477885
0.9205	High Similarity	NPC475592
0.92	High Similarity	NPC117154
0.9189	High Similarity	NPC475756
0.9149	High Similarity	NPC32189
0.9149	High Similarity	NPC11453
0.9145	High Similarity	NPC325122
0.9128	High Similarity	NPC471154
0.9091	High Similarity	NPC216434
0.9091	High Similarity	NPC103448
0.9085	High Similarity	NPC865
0.9067	High Similarity	NPC474606
0.9048	High Similarity	NPC295297
0.9041	High Similarity	NPC475868
0.9026	High Similarity	NPC319749
0.902	High Similarity	NPC215400
0.902	High Similarity	NPC230531
0.9007	High Similarity	NPC185680
0.9007	High Similarity	NPC145722
0.9007	High Similarity	NPC473425
0.9007	High Similarity	NPC256776
0.8981	High Similarity	NPC79322
0.8973	High Similarity	NPC172171
0.8973	High Similarity	NPC475000
0.8973	High Similarity	NPC239254
0.8968	High Similarity	NPC61141
0.8968	High Similarity	NPC280778
0.8966	High Similarity	NPC474295
0.8966	High Similarity	NPC287124
0.8947	High Similarity	NPC238834
0.894	High Similarity	NPC474514
0.8933	High Similarity	NPC210642
0.8933	High Similarity	NPC13985
0.8926	High Similarity	NPC474347
0.8926	High Similarity	NPC474393
0.8904	High Similarity	NPC324962
0.8889	High Similarity	NPC29727
0.8882	High Similarity	NPC273578
0.8881	High Similarity	NPC143895
0.8874	High Similarity	NPC104353
0.8867	High Similarity	NPC149505
0.8867	High Similarity	NPC470916
0.8867	High Similarity	NPC477381
0.8865	High Similarity	NPC65183
0.8865	High Similarity	NPC261812
0.8865	High Similarity	NPC72046
0.8854	High Similarity	NPC477884
0.8851	High Similarity	NPC193779
0.8851	High Similarity	NPC252286
0.8851	High Similarity	NPC154971
0.8844	High Similarity	NPC141569
0.8844	High Similarity	NPC166884
0.8844	High Similarity	NPC477701
0.8836	High Similarity	NPC230538
0.8836	High Similarity	NPC151423
0.8836	High Similarity	NPC36531
0.8836	High Similarity	NPC40237
0.8836	High Similarity	NPC229172
0.8836	High Similarity	NPC103637
0.8811	High Similarity	NPC148893
0.8811	High Similarity	NPC49235
0.8811	High Similarity	NPC25333
0.8808	High Similarity	NPC477379
0.8803	High Similarity	NPC136750
0.8803	High Similarity	NPC266848
0.8797	High Similarity	NPC118162
0.8797	High Similarity	NPC83049
0.8797	High Similarity	NPC320471
0.8792	High Similarity	NPC137352
0.8792	High Similarity	NPC183083
0.879	High Similarity	NPC475865
0.8784	High Similarity	NPC474158
0.8784	High Similarity	NPC477702
0.8767	High Similarity	NPC312199
0.8759	High Similarity	NPC290714
0.8759	High Similarity	NPC201404
0.8759	High Similarity	NPC53722
0.875	High Similarity	NPC121651
0.875	High Similarity	NPC220577
0.8742	High Similarity	NPC311912
0.8741	High Similarity	NPC31530
0.8733	High Similarity	NPC262804
0.8733	High Similarity	NPC40654
0.8732	High Similarity	NPC7744
0.8725	High Similarity	NPC87295
0.8725	High Similarity	NPC212890
0.8718	High Similarity	NPC474770
0.8718	High Similarity	NPC63061
0.8716	High Similarity	NPC218841
0.8716	High Similarity	NPC87883
0.8716	High Similarity	NPC143092
0.8716	High Similarity	NPC121661
0.8716	High Similarity	NPC474036
0.8716	High Similarity	NPC92693
0.8716	High Similarity	NPC18211
0.8716	High Similarity	NPC73467
0.871	High Similarity	NPC19947
0.871	High Similarity	NPC207584
0.8707	High Similarity	NPC210354
0.8707	High Similarity	NPC176586
0.8693	High Similarity	NPC149735
0.8688	High Similarity	NPC88557
0.8681	High Similarity	NPC474139
0.8681	High Similarity	NPC189474
0.8667	High Similarity	NPC104024
0.8667	High Similarity	NPC65574
0.8667	High Similarity	NPC101755
0.8667	High Similarity	NPC304687
0.8667	High Similarity	NPC80230
0.8662	High Similarity	NPC141493
0.8662	High Similarity	NPC184928
0.8662	High Similarity	NPC192255
0.8658	High Similarity	NPC166506
0.8658	High Similarity	NPC110763
0.8658	High Similarity	NPC197352
0.8658	High Similarity	NPC189239
0.8654	High Similarity	NPC474043
0.8649	High Similarity	NPC474288
0.8645	High Similarity	NPC32373
0.8645	High Similarity	NPC237946
0.8642	High Similarity	NPC474568
0.8634	High Similarity	NPC477883
0.863	High Similarity	NPC113550
0.8625	High Similarity	NPC42230
0.8618	High Similarity	NPC24425
0.8616	High Similarity	NPC475953
0.8609	High Similarity	NPC304821
0.8609	High Similarity	NPC477879
0.8601	High Similarity	NPC475856
0.86	High Similarity	NPC474054
0.8599	High Similarity	NPC96593
0.8591	High Similarity	NPC50696
0.8591	High Similarity	NPC191158
0.8591	High Similarity	NPC177644
0.8582	High Similarity	NPC54321
0.8582	High Similarity	NPC328682
0.8582	High Similarity	NPC281864
0.8581	High Similarity	NPC184684
0.8581	High Similarity	NPC80326
0.8581	High Similarity	NPC472562
0.8581	High Similarity	NPC184641
0.8581	High Similarity	NPC133934
0.858	High Similarity	NPC178737
0.8571	High Similarity	NPC46591
0.8571	High Similarity	NPC475141
0.8562	High Similarity	NPC32079
0.8562	High Similarity	NPC477700
0.8562	High Similarity	NPC283949
0.8562	High Similarity	NPC166184
0.8562	High Similarity	NPC196420
0.8553	High Similarity	NPC177476
0.8553	High Similarity	NPC469475
0.8553	High Similarity	NPC477698
0.8553	High Similarity	NPC469518
0.8553	High Similarity	NPC262455
0.8552	High Similarity	NPC150534
0.8544	High Similarity	NPC288149
0.8542	High Similarity	NPC1474
0.8528	High Similarity	NPC477881
0.8521	High Similarity	NPC476748

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 NPC85141 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	314
0.1-0.2	943
0.2-0.3	1814
0.3-0.4	2872
0.4-0.5	1694
0.5-0.6	971
0.6-0.7	466
0.7-0.8	68
0.8-0.85	5
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8645	High Similarity	NPD4965	Approved
0.8645	High Similarity	NPD4966	Approved
0.8645	High Similarity	NPD4967	Phase 2
0.8535	High Similarity	NPD6234	Discontinued
0.8452	Intermediate Similarity	NPD37	Approved
0.8199	Intermediate Similarity	NPD7199	Phase 2
0.8171	Intermediate Similarity	NPD7228	Approved
0.8129	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8098	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.8085	Intermediate Similarity	NPD3705	Approved
0.7976	Intermediate Similarity	NPD7240	Approved
0.7736	Intermediate Similarity	NPD1653	Approved
0.7707	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7633	Intermediate Similarity	NPD3818	Discontinued
0.759	Intermediate Similarity	NPD5494	Approved
0.7588	Intermediate Similarity	NPD5844	Phase 1
0.7533	Intermediate Similarity	NPD3027	Phase 3
0.7515	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6232	Discontinued
0.7486	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD7473	Discontinued
0.7455	Intermediate Similarity	NPD3817	Phase 2
0.7436	Intermediate Similarity	NPD7266	Discontinued
0.7429	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD3018	Phase 2
0.7394	Intermediate Similarity	NPD1465	Phase 2
0.7356	Intermediate Similarity	NPD6559	Discontinued
0.7342	Intermediate Similarity	NPD6674	Discontinued
0.7341	Intermediate Similarity	NPD7074	Phase 3
0.7324	Intermediate Similarity	NPD5283	Phase 1
0.7322	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD919	Approved
0.7308	Intermediate Similarity	NPD3748	Approved
0.7297	Intermediate Similarity	NPD2981	Phase 2
0.7297	Intermediate Similarity	NPD5005	Approved
0.7297	Intermediate Similarity	NPD5006	Approved
0.7289	Intermediate Similarity	NPD7819	Suspended
0.7284	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD7054	Approved
0.7273	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD1613	Approved
0.7261	Intermediate Similarity	NPD2438	Suspended
0.726	Intermediate Similarity	NPD5691	Approved
0.7251	Intermediate Similarity	NPD3926	Phase 2
0.7248	Intermediate Similarity	NPD2983	Phase 2
0.7248	Intermediate Similarity	NPD2982	Phase 2
0.7241	Intermediate Similarity	NPD7472	Approved
0.7241	Intermediate Similarity	NPD5536	Phase 2
0.7229	Intermediate Similarity	NPD1934	Approved
0.7216	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD3882	Suspended
0.7174	Intermediate Similarity	NPD4420	Approved
0.7171	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7166	Intermediate Similarity	NPD7680	Approved
0.7161	Intermediate Similarity	NPD4060	Phase 1
0.716	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD5242	Approved
0.7143	Intermediate Similarity	NPD5353	Approved
0.7143	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD8127	Discontinued
0.7124	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD7808	Phase 3
0.7117	Intermediate Similarity	NPD2532	Approved
0.7117	Intermediate Similarity	NPD2534	Approved
0.7117	Intermediate Similarity	NPD2533	Approved
0.7115	Intermediate Similarity	NPD1933	Approved
0.7111	Intermediate Similarity	NPD6843	Phase 3
0.7111	Intermediate Similarity	NPD6842	Approved
0.7111	Intermediate Similarity	NPD6841	Approved
0.7102	Intermediate Similarity	NPD6797	Phase 2
0.7093	Intermediate Similarity	NPD7229	Phase 3
0.7083	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD3750	Approved
0.7072	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD7251	Discontinued
0.7062	Intermediate Similarity	NPD7685	Pre-registration
0.7059	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD6799	Approved
0.7051	Intermediate Similarity	NPD2979	Phase 3
0.7048	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD2796	Approved
0.7037	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD1247	Approved
0.7022	Intermediate Similarity	NPD7549	Discontinued
0.7013	Intermediate Similarity	NPD4908	Phase 1
0.7011	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD6166	Phase 2
0.7011	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD6599	Discontinued
0.7006	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD7028	Phase 2
0.7006	Intermediate Similarity	NPD6355	Discontinued
0.7	Intermediate Similarity	NPD5762	Approved
0.7	Intermediate Similarity	NPD5763	Approved
0.6982	Remote Similarity	NPD8455	Phase 2
0.6982	Remote Similarity	NPD2801	Approved
0.6982	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.698	Remote Similarity	NPD4626	Approved
0.6975	Remote Similarity	NPD4110	Phase 3
0.6975	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD5089	Approved
0.6964	Remote Similarity	NPD5090	Approved
0.6959	Remote Similarity	NPD7075	Discontinued
0.6951	Remote Similarity	NPD4357	Discontinued
0.6941	Remote Similarity	NPD5402	Approved
0.6937	Remote Similarity	NPD3539	Phase 1
0.6932	Remote Similarity	NPD3751	Discontinued
0.6928	Remote Similarity	NPD920	Approved
0.6923	Remote Similarity	NPD6801	Discontinued
0.6923	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD1652	Phase 2
0.6914	Remote Similarity	NPD1243	Approved
0.6913	Remote Similarity	NPD1357	Approved
0.6908	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD4380	Phase 2
0.6901	Remote Similarity	NPD1358	Approved
0.6899	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD230	Phase 1
0.6899	Remote Similarity	NPD5124	Phase 1
0.6897	Remote Similarity	NPD3787	Discontinued
0.6894	Remote Similarity	NPD3540	Phase 1
0.6887	Remote Similarity	NPD422	Phase 1
0.6887	Remote Similarity	NPD1611	Approved
0.6887	Remote Similarity	NPD1281	Approved
0.6887	Remote Similarity	NPD1610	Phase 2
0.6882	Remote Similarity	NPD5563	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD4585	Approved
0.6871	Remote Similarity	NPD4628	Phase 3
0.6864	Remote Similarity	NPD6385	Approved
0.6864	Remote Similarity	NPD6386	Approved
0.6859	Remote Similarity	NPD4625	Phase 3
0.6842	Remote Similarity	NPD6374	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD2861	Phase 2
0.6839	Remote Similarity	NPD6959	Discontinued
0.6832	Remote Similarity	NPD2935	Discontinued
0.6831	Remote Similarity	NPD3134	Approved
0.6829	Remote Similarity	NPD6190	Approved
0.6826	Remote Similarity	NPD5403	Approved
0.6818	Remote Similarity	NPD4481	Phase 3
0.6813	Remote Similarity	NPD7097	Phase 1
0.6811	Remote Similarity	NPD7296	Approved
0.6811	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD5401	Approved
0.6807	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD7768	Phase 2
0.68	Remote Similarity	NPD5585	Approved
0.6798	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD8313	Approved
0.6796	Remote Similarity	NPD8312	Approved
0.6795	Remote Similarity	NPD6832	Phase 2
0.6795	Remote Similarity	NPD1008	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD3657	Discovery
0.6788	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD7124	Phase 2
0.6776	Remote Similarity	NPD1091	Approved
0.6774	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.677	Remote Similarity	NPD4108	Discontinued
0.6768	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD7411	Suspended
0.6763	Remote Similarity	NPD3749	Approved
0.6763	Remote Similarity	NPD4055	Discovery
0.6755	Remote Similarity	NPD17	Approved
0.6753	Remote Similarity	NPD1283	Approved
0.6747	Remote Similarity	NPD1511	Approved
0.6747	Remote Similarity	NPD5297	Approved
0.6746	Remote Similarity	NPD4005	Discontinued
0.6746	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD7458	Discontinued
0.673	Remote Similarity	NPD4140	Approved
0.673	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.673	Remote Similarity	NPD3620	Phase 2
0.6728	Remote Similarity	NPD2531	Phase 2
0.6725	Remote Similarity	NPD3384	Approved
0.6725	Remote Similarity	NPD3383	Approved
0.6725	Remote Similarity	NPD3382	Approved
0.6718	Remote Similarity	NPD8151	Discontinued
0.6711	Remote Similarity	NPD3496	Discontinued
0.671	Remote Similarity	NPD3266	Approved
0.671	Remote Similarity	NPD3267	Approved
0.671	Remote Similarity	NPD2797	Approved
0.6709	Remote Similarity	NPD1296	Phase 2
0.6709	Remote Similarity	NPD5109	Approved
0.6709	Remote Similarity	NPD5110	Phase 2
0.6709	Remote Similarity	NPD5111	Phase 2
0.6709	Remote Similarity	NPD6798	Discontinued
0.6708	Remote Similarity	NPD6111	Discontinued
0.6707	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD7235	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD1651	Approved
0.6688	Remote Similarity	NPD4749	Approved
0.6687	Remote Similarity	NPD6002	Phase 3
0.6687	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD447	Suspended
0.6687	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD6005	Phase 3

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