NPASS Compound

Structure

NPC295297 OpenBabel07101719252D 38 40 0 0 1 0 0 0 0 0999 V2000 -1.9263 2.5237 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3131 0.4199 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3168 0.8799 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7556 0.5798 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9587 -3.9587 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0063 -3.9587 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2852 -4.6321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7395 -5.0590 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0985 -5.4860 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8539 -5.4860 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6818 1.9440 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6258 -0.6734 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5457 -1.8723 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5934 -1.8723 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5575 0.9997 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9524 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6258 -1.6258 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6734 -1.6258 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7922 -2.7922 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8399 -2.7922 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9524 -2.2993 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.2993 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1188 -3.4657 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1664 -3.4657 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1989 -3.2192 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2465 -3.2192 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6734 -0.6734 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6776 0.6353 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9221 1.2150 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1243 0.9442 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7122 -3.0387 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7598 -3.0387 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3653 -4.3856 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4129 -4.3856 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1480 -4.5661 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1004 -4.5661 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5533 -0.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 11 1 0 0 0 0 2 15 1 0 0 0 0 3 16 1 0 0 0 0 5 32 1 0 0 0 0 6 33 1 0 0 0 0 7 34 1 0 0 0 0 8 35 1 0 0 0 0 9 36 1 0 0 0 0 10 37 1 0 0 0 0 11 15 2 0 0 0 0 12 16 1 0 0 0 0 12 17 1 0 0 0 0 13 17 2 0 0 0 0 13 19 1 0 0 0 0 14 18 2 0 0 0 0 14 20 1 0 0 0 0 15 28 1 0 0 0 0 16 29 1 1 0 0 0 17 21 1 0 0 0 0 18 22 1 0 0 0 0 18 27 1 0 0 0 0 19 23 2 0 0 0 0 19 32 1 0 0 0 0 20 24 2 0 0 0 0 20 33 1 0 0 0 0 21 22 1 0 0 0 0 21 25 2 0 0 0 0 22 26 2 0 0 0 0 23 25 1 0 0 0 0 23 34 1 0 0 0 0 24 26 1 0 0 0 0 24 35 1 0 0 0 0 25 36 1 0 0 0 0 26 37 1 0 0 0 0 27 29 1 6 0 0 0 27 38 1 0 0 0 0 28 30 2 0 0 0 0 28 38 1 0 0 0 0 29 4 1 6 0 0 0 29 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	530.25
Volume:	542.491
LogP:	3.71
LogD:	3.136
LogS:	-4.404
# Rotatable Bonds:	9
TPSA:	101.91
# H-Bond Aceptor:	9
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.377
Synthetic Accessibility Score:	4.003
Fsp3:	0.483
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:	-4.618
MDCK Permeability:	2.202860741817858e-05
Pgp-inhibitor:	0.997
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.096

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.058
Plasma Protein Binding (PPB):	61.98978042602539%
Volume Distribution (VD):	0.744
Pgp-substrate:	29.547855377197266%

ADMET: Metabolism

CYP1A2-inhibitor:	0.048
CYP1A2-substrate:	0.989
CYP2C19-inhibitor:	0.585
CYP2C19-substrate:	0.936
CYP2C9-inhibitor:	0.478
CYP2C9-substrate:	0.802
CYP2D6-inhibitor:	0.015
CYP2D6-substrate:	0.857
CYP3A4-inhibitor:	0.853
CYP3A4-substrate:	0.904

ADMET: Excretion

Clearance (CL):	6.069
Half-life (T1/2):	0.111

ADMET: Toxicity

hERG Blockers:	0.209
Human Hepatotoxicity (H-HT):	0.074
Drug-inuced Liver Injury (DILI):	0.408
AMES Toxicity:	0.052
Rat Oral Acute Toxicity:	0.286
Maximum Recommended Daily Dose:	0.045
Skin Sensitization:	0.169
Carcinogencity:	0.021
Eye Corrosion:	0.003
Eye Irritation:	0.155
Respiratory Toxicity:	0.707

Download Data

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

Natural Product: NPC295297

Natural Product ID:	NPC295297
*Common Name:**	RHABJANPSGWEFC-MRFZJNLZSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	RHABJANPSGWEFC-MRFZJNLZSA-N
Standard InCHI:	InChI=1S/C29H38O9/c1-11-15(2)28(30)38-27-18-14-20(33-6)24(35-8)26(37-10)22(18)21-17(12-16(3)29(27,4)31)13-19(32-5)23(34-7)25(21)36-9/h11,13-14,16,27,31H,12H2,1-10H3/b15-11-/t16-,27-,29-/m0/s1
SMILES:	C/C=C(C(=O)O[C@H]1c2cc(OC)c(c(c2c2c(C[C@@H]([C@]1(C)O)C)cc(c(c2OC)OC)OC)OC)OC)/C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2386337
PubChem CID:	14992071
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
NPO29191	Schisandra neglecta	Species	Schisandraceae	Eukaryota	Stems	Luoji Mountain Village, Xichang County, Sicuan Province, China	2011-Sep	PMID[23738539]
NPO29191	Schisandra neglecta	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
IC50	5
Others	2

Activity Type	# Activity
Cell Line	5
NON-MOLECULAR	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	=	84700.0	nM	PMID[553251]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	10000.0	nM	PMID[553251]
NPT306	Cell Line	PC-3	Homo sapiens	IC50	>	10000.0	nM	PMID[553251]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[553251]
NPT2678	Cell Line	NB-4	Homo sapiens	IC50	>	10000.0	nM	PMID[553251]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	11500.0	nM	PMID[553251]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	7800.0	nM	PMID[553251]
NPT27	Others	Unspecified		Ratio CC50/EC50	=	7.4	n.a.	PMID[553251]

☑ 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 NPC295297 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	1325
0.2-0.3	3361
0.3-0.4	7774
0.4-0.5	10628
0.5-0.6	3904
0.6-0.7	7065
0.7-0.8	7404
0.8-0.85	744
0.85-0.9	114
0.9-0.95	36
0.95-1	14

Similarity Score	Similarity Level	Natural Product ID
0.9789	High Similarity	NPC470916
0.9718	High Similarity	NPC474347
0.9718	High Similarity	NPC474393
0.9586	High Similarity	NPC16791
0.9586	High Similarity	NPC126405
0.9586	High Similarity	NPC53669
0.9586	High Similarity	NPC217708
0.9586	High Similarity	NPC77237
0.9586	High Similarity	NPC308739
0.9586	High Similarity	NPC297271
0.9577	High Similarity	NPC183083
0.9577	High Similarity	NPC137352
0.9514	High Similarity	NPC477381
0.9452	High Similarity	NPC149735
0.9448	High Similarity	NPC477379
0.9448	High Similarity	NPC224472
0.9388	High Similarity	NPC473736
0.9388	High Similarity	NPC198461
0.9371	High Similarity	NPC474054
0.9366	High Similarity	NPC87883
0.9353	High Similarity	NPC865
0.9329	High Similarity	NPC475592
0.9324	High Similarity	NPC476065
0.932	High Similarity	NPC475141
0.932	High Similarity	NPC24562
0.9241	High Similarity	NPC252281
0.9241	High Similarity	NPC327352
0.9241	High Similarity	NPC477375
0.9241	High Similarity	NPC198129
0.9241	High Similarity	NPC477879
0.9178	High Similarity	NPC322426
0.9178	High Similarity	NPC477374
0.9178	High Similarity	NPC477376
0.9133	High Similarity	NPC473323
0.9128	High Similarity	NPC312763
0.9122	High Similarity	NPC471154
0.9116	High Similarity	NPC316989
0.9085	High Similarity	NPC42797
0.906	High Similarity	NPC474606
0.9054	High Similarity	NPC475756
0.9048	High Similarity	NPC85141
0.9034	High Similarity	NPC318286
0.9034	High Similarity	NPC327651
0.9026	High Similarity	NPC291977
0.9014	High Similarity	NPC471183
0.9013	High Similarity	NPC215400
0.9013	High Similarity	NPC230531
0.9007	High Similarity	NPC29727
0.8993	High Similarity	NPC102256
0.898	High Similarity	NPC325720
0.898	High Similarity	NPC316676
0.8973	High Similarity	NPC321958
0.8973	High Similarity	NPC321696
0.8966	High Similarity	NPC326144
0.8961	High Similarity	NPC473445
0.894	High Similarity	NPC238834
0.8933	High Similarity	NPC477377
0.8921	High Similarity	NPC184928
0.8921	High Similarity	NPC141493
0.891	High Similarity	NPC83049
0.891	High Similarity	NPC320471
0.891	High Similarity	NPC118162
0.8897	High Similarity	NPC218510
0.8897	High Similarity	NPC76415
0.8889	High Similarity	NPC328122
0.8874	High Similarity	NPC473425
0.8873	High Similarity	NPC133025
0.8867	High Similarity	NPC477378
0.8867	High Similarity	NPC475229
0.8859	High Similarity	NPC473989
0.8839	High Similarity	NPC249070
0.8811	High Similarity	NPC156948
0.8811	High Similarity	NPC3072
0.8811	High Similarity	NPC301765
0.8811	High Similarity	NPC86605
0.8811	High Similarity	NPC46277
0.8803	High Similarity	NPC214853
0.8803	High Similarity	NPC55239
0.8803	High Similarity	NPC180602
0.8803	High Similarity	NPC240279
0.8767	High Similarity	NPC469630
0.8758	High Similarity	NPC477380
0.8758	High Similarity	NPC469474
0.875	High Similarity	NPC348849
0.875	High Similarity	NPC178195
0.8734	High Similarity	NPC79322
0.8732	High Similarity	NPC469659
0.8732	High Similarity	NPC56764
0.8732	High Similarity	NPC188378
0.8732	High Similarity	NPC276026
0.8732	High Similarity	NPC555
0.8732	High Similarity	NPC289258
0.8732	High Similarity	NPC7515
0.8732	High Similarity	NPC206737
0.8725	High Similarity	NPC252402
0.8725	High Similarity	NPC102934
0.871	High Similarity	NPC63061
0.8705	High Similarity	NPC149008
0.8705	High Similarity	NPC283114
0.8705	High Similarity	NPC207702
0.8701	High Similarity	NPC477885
0.8679	High Similarity	NPC88557
0.8658	High Similarity	NPC178129
0.8639	High Similarity	NPC324962
0.8625	High Similarity	NPC477883
0.8621	High Similarity	NPC53722
0.8621	High Similarity	NPC290714
0.8621	High Similarity	NPC201404
0.8616	High Similarity	NPC311912
0.8611	High Similarity	NPC471719
0.8591	High Similarity	NPC205361
0.8581	High Similarity	NPC121661
0.8581	High Similarity	NPC143092
0.8581	High Similarity	NPC18211
0.8581	High Similarity	NPC73467
0.8571	High Similarity	NPC36531
0.8571	High Similarity	NPC229172
0.8571	High Similarity	NPC230538
0.8571	High Similarity	NPC103637
0.8553	High Similarity	NPC303519
0.8535	High Similarity	NPC319749
0.8533	High Similarity	NPC15577
0.8526	High Similarity	NPC325122
0.8523	High Similarity	NPC110763
0.8523	High Similarity	NPC189239
0.8523	High Similarity	NPC475868
0.8523	High Similarity	NPC197352
0.8523	High Similarity	NPC166506
0.8519	High Similarity	NPC477881
0.8503	High Similarity	NPC300611
0.8497	Intermediate Similarity	NPC272566
0.8497	Intermediate Similarity	NPC476434
0.8497	Intermediate Similarity	NPC228662
0.8487	Intermediate Similarity	NPC24425
0.8483	Intermediate Similarity	NPC471988
0.8481	Intermediate Similarity	NPC280778
0.8481	Intermediate Similarity	NPC469512
0.8477	Intermediate Similarity	NPC93924
0.8477	Intermediate Similarity	NPC476348
0.8477	Intermediate Similarity	NPC187398
0.8472	Intermediate Similarity	NPC309744
0.8472	Intermediate Similarity	NPC135127
0.8471	Intermediate Similarity	NPC24627
0.8467	Intermediate Similarity	NPC40222
0.8467	Intermediate Similarity	NPC252286
0.8467	Intermediate Similarity	NPC154971
0.8467	Intermediate Similarity	NPC268515
0.8462	Intermediate Similarity	NPC475856
0.8462	Intermediate Similarity	NPC125495
0.8456	Intermediate Similarity	NPC239254
0.8456	Intermediate Similarity	NPC172171
0.8452	Intermediate Similarity	NPC476642
0.8451	Intermediate Similarity	NPC79184
0.8451	Intermediate Similarity	NPC476399
0.8451	Intermediate Similarity	NPC307042
0.8446	Intermediate Similarity	NPC184641
0.8446	Intermediate Similarity	NPC133934
0.8446	Intermediate Similarity	NPC184684
0.8446	Intermediate Similarity	NPC67467
0.8446	Intermediate Similarity	NPC287124
0.8442	Intermediate Similarity	NPC65591
0.8442	Intermediate Similarity	NPC178574
0.8428	Intermediate Similarity	NPC469518
0.8428	Intermediate Similarity	NPC469475
0.8425	Intermediate Similarity	NPC281780
0.8421	Intermediate Similarity	NPC176903
0.8421	Intermediate Similarity	NPC30688
0.8418	Intermediate Similarity	NPC258322
0.8418	Intermediate Similarity	NPC191352
0.8414	Intermediate Similarity	NPC311430
0.8414	Intermediate Similarity	NPC224941
0.8411	Intermediate Similarity	NPC476347
0.8408	Intermediate Similarity	NPC241600
0.8408	Intermediate Similarity	NPC173726
0.84	Intermediate Similarity	NPC163898
0.84	Intermediate Similarity	NPC477702
0.8389	Intermediate Similarity	NPC470811
0.8389	Intermediate Similarity	NPC477697
0.8389	Intermediate Similarity	NPC6568
0.8389	Intermediate Similarity	NPC477696
0.8389	Intermediate Similarity	NPC138212
0.8377	Intermediate Similarity	NPC95498
0.8377	Intermediate Similarity	NPC302610
0.8377	Intermediate Similarity	NPC246566
0.8375	Intermediate Similarity	NPC477884
0.8369	Intermediate Similarity	NPC242032
0.8367	Intermediate Similarity	NPC230124
0.8367	Intermediate Similarity	NPC6300
0.8367	Intermediate Similarity	NPC114171
0.8366	Intermediate Similarity	NPC294522
0.8366	Intermediate Similarity	NPC21184
0.8366	Intermediate Similarity	NPC120426
0.8366	Intermediate Similarity	NPC205727
0.8364	Intermediate Similarity	NPC477882
0.8364	Intermediate Similarity	NPC477880
0.8356	Intermediate Similarity	NPC143895
0.8355	Intermediate Similarity	NPC304821
0.8355	Intermediate Similarity	NPC473408
0.8355	Intermediate Similarity	NPC236166
0.8345	Intermediate Similarity	NPC145722

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 NPC295297 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	278
0.1-0.2	874
0.2-0.3	1797
0.3-0.4	2660
0.4-0.5	1795
0.5-0.6	1028
0.6-0.7	573
0.7-0.8	137
0.8-0.85	8
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8205	Intermediate Similarity	NPD37	Approved
0.8176	Intermediate Similarity	NPD6234	Discontinued
0.8165	Intermediate Similarity	NPD4966	Approved
0.8165	Intermediate Similarity	NPD4967	Phase 2
0.8165	Intermediate Similarity	NPD4965	Approved
0.8125	Intermediate Similarity	NPD3027	Phase 3
0.805	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD5844	Phase 1
0.7988	Intermediate Similarity	NPD7473	Discontinued
0.7963	Intermediate Similarity	NPD7199	Phase 2
0.7939	Intermediate Similarity	NPD7228	Approved
0.7925	Intermediate Similarity	NPD1465	Phase 2
0.7914	Intermediate Similarity	NPD6232	Discontinued
0.7875	Intermediate Similarity	NPD3817	Phase 2
0.7866	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7838	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7838	Intermediate Similarity	NPD1613	Approved
0.7834	Intermediate Similarity	NPD1653	Approved
0.7812	Intermediate Similarity	NPD7819	Suspended
0.7751	Intermediate Similarity	NPD7240	Approved
0.775	Intermediate Similarity	NPD1934	Approved
0.774	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7718	Intermediate Similarity	NPD4060	Phase 1
0.7703	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7687	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD7266	Discontinued
0.7619	Intermediate Similarity	NPD3018	Phase 2
0.7613	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7572	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD7075	Discontinued
0.755	Intermediate Similarity	NPD6355	Discontinued
0.7548	Intermediate Similarity	NPD6674	Discontinued
0.7547	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD5763	Approved
0.7532	Intermediate Similarity	NPD5762	Approved
0.753	Intermediate Similarity	NPD8127	Discontinued
0.7529	Intermediate Similarity	NPD7074	Phase 3
0.7515	Intermediate Similarity	NPD3818	Discontinued
0.75	Intermediate Similarity	NPD3882	Suspended
0.75	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7549	Discontinued
0.75	Intermediate Similarity	NPD3750	Approved
0.75	Intermediate Similarity	NPD6166	Phase 2
0.75	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD2801	Approved
0.7471	Intermediate Similarity	NPD7054	Approved
0.747	Intermediate Similarity	NPD5494	Approved
0.7468	Intermediate Similarity	NPD6799	Approved
0.7466	Intermediate Similarity	NPD2983	Phase 2
0.7466	Intermediate Similarity	NPD2982	Phase 2
0.7466	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD6190	Approved
0.745	Intermediate Similarity	NPD4908	Phase 1
0.7448	Intermediate Similarity	NPD3705	Approved
0.7436	Intermediate Similarity	NPD1652	Phase 2
0.7434	Intermediate Similarity	NPD5124	Phase 1
0.7434	Intermediate Similarity	NPD230	Phase 1
0.7434	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD5283	Phase 1
0.7427	Intermediate Similarity	NPD7472	Approved
0.7407	Intermediate Similarity	NPD6599	Discontinued
0.7407	Intermediate Similarity	NPD4380	Phase 2
0.7403	Intermediate Similarity	NPD3748	Approved
0.74	Intermediate Similarity	NPD4625	Phase 3
0.74	Intermediate Similarity	NPD7095	Approved
0.7397	Intermediate Similarity	NPD2981	Phase 2
0.7389	Intermediate Similarity	NPD4628	Phase 3
0.7381	Intermediate Similarity	NPD7229	Phase 3
0.7361	Intermediate Similarity	NPD5691	Approved
0.7358	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD2438	Suspended
0.7351	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7343	Intermediate Similarity	NPD5536	Phase 2
0.7333	Intermediate Similarity	NPD5353	Approved
0.7333	Intermediate Similarity	NPD5402	Approved
0.7329	Intermediate Similarity	NPD1610	Phase 2
0.7329	Intermediate Similarity	NPD422	Phase 1
0.7317	Intermediate Similarity	NPD6801	Discontinued
0.7315	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD2534	Approved
0.7312	Intermediate Similarity	NPD2533	Approved
0.7312	Intermediate Similarity	NPD2532	Approved
0.731	Intermediate Similarity	NPD4626	Approved
0.7299	Intermediate Similarity	NPD7808	Phase 3
0.7299	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD7768	Phase 2
0.7288	Intermediate Similarity	NPD6842	Approved
0.7288	Intermediate Similarity	NPD6843	Phase 3
0.7288	Intermediate Similarity	NPD6841	Approved
0.7278	Intermediate Similarity	NPD4110	Phase 3
0.7278	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD5089	Approved
0.7256	Intermediate Similarity	NPD5090	Approved
0.725	Intermediate Similarity	NPD4357	Discontinued
0.725	Intermediate Similarity	NPD1511	Approved
0.7246	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD2935	Discontinued
0.7244	Intermediate Similarity	NPD6099	Approved
0.7244	Intermediate Similarity	NPD6100	Approved
0.7241	Intermediate Similarity	NPD7251	Discontinued
0.7241	Intermediate Similarity	NPD7685	Pre-registration
0.7241	Intermediate Similarity	NPD6559	Discontinued
0.7237	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD6798	Discontinued
0.7235	Intermediate Similarity	NPD5242	Approved
0.723	Intermediate Similarity	NPD4749	Approved
0.7226	Intermediate Similarity	NPD7097	Phase 1
0.7222	Intermediate Similarity	NPD5403	Approved
0.7219	Intermediate Similarity	NPD6959	Discontinued
0.7216	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD3751	Discontinued
0.7205	Intermediate Similarity	NPD5401	Approved
0.7202	Intermediate Similarity	NPD919	Approved
0.7184	Intermediate Similarity	NPD6797	Phase 2
0.7181	Intermediate Similarity	NPD1283	Approved
0.7176	Intermediate Similarity	NPD3787	Discontinued
0.7169	Intermediate Similarity	NPD8455	Phase 2
0.716	Intermediate Similarity	NPD1512	Approved
0.7152	Intermediate Similarity	NPD7411	Suspended
0.7152	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD2861	Phase 2
0.7143	Intermediate Similarity	NPD2979	Phase 3
0.7143	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3620	Phase 2
0.7135	Intermediate Similarity	NPD8434	Phase 2
0.7135	Intermediate Similarity	NPD3926	Phase 2
0.7134	Intermediate Similarity	NPD4005	Discontinued
0.7134	Intermediate Similarity	NPD2796	Approved
0.7134	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD2797	Approved
0.7126	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD447	Suspended
0.7089	Intermediate Similarity	NPD3540	Phase 1
0.7078	Intermediate Similarity	NPD6233	Phase 2
0.7072	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD1510	Phase 2
0.7063	Intermediate Similarity	NPD8166	Discontinued
0.7063	Intermediate Similarity	NPD7982	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD1548	Phase 1
0.7051	Intermediate Similarity	NPD6653	Approved
0.7048	Intermediate Similarity	NPD6386	Approved
0.7048	Intermediate Similarity	NPD6385	Approved
0.7047	Intermediate Similarity	NPD1608	Approved
0.7044	Intermediate Similarity	NPD1549	Phase 2
0.7044	Intermediate Similarity	NPD2424	Discontinued
0.7041	Intermediate Similarity	NPD3749	Approved
0.7041	Intermediate Similarity	NPD4055	Discovery
0.7032	Intermediate Similarity	NPD4140	Approved
0.7032	Intermediate Similarity	NPD1240	Approved
0.703	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD3496	Discontinued
0.7025	Intermediate Similarity	NPD6032	Approved
0.7025	Intermediate Similarity	NPD3539	Phase 1
0.7025	Intermediate Similarity	NPD1551	Phase 2
0.7024	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD3268	Approved
0.7013	Intermediate Similarity	NPD7985	Registered
0.7	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1358	Approved
0.7	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD6832	Phase 2
0.6981	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.698	Remote Similarity	NPD1281	Approved
0.698	Remote Similarity	NPD1611	Approved
0.6975	Remote Similarity	NPD7124	Phase 2
0.6971	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD7680	Approved
0.6966	Remote Similarity	NPD7157	Approved
0.6966	Remote Similarity	NPD8312	Approved
0.6966	Remote Similarity	NPD8313	Approved
0.6964	Remote Similarity	NPD4585	Approved
0.6962	Remote Similarity	NPD7033	Discontinued
0.6962	Remote Similarity	NPD2799	Discontinued
0.6957	Remote Similarity	NPD3892	Phase 2
0.6957	Remote Similarity	NPD7003	Approved
0.6951	Remote Similarity	NPD6273	Approved
0.6943	Remote Similarity	NPD1607	Approved
0.6929	Remote Similarity	NPD3134	Approved
0.6928	Remote Similarity	NPD3226	Approved
0.6923	Remote Similarity	NPD228	Approved
0.6923	Remote Similarity	NPD2238	Phase 2
0.6919	Remote Similarity	NPD1247	Approved
0.6914	Remote Similarity	NPD2677	Approved
0.6903	Remote Similarity	NPD3764	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