NPASS Compound

Structure

CID24562 OpenBabel06191715352D 37 40 0 0 1 0 0 0 0 0999 V2000 9.0054 0.3605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4942 -0.7991 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5456 2.8000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7345 1.6111 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1812 -3.6783 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8002 -2.8535 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3716 -2.0287 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9058 -2.5628 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1255 0.7249 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7306 1.7229 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6573 -1.2039 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5598 0.7705 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3699 0.1452 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1812 1.9201 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.8546 1.2467 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5553 1.2467 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1812 -0.3791 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1812 -2.0287 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9058 1.2467 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5553 0.2943 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2288 -0.3791 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2288 1.9201 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.8546 0.2943 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.2288 -2.0287 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9058 0.2943 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7526 -1.2039 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7306 -0.1819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4901 0.5096 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8643 2.8000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3657 1.4538 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6573 -2.8535 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7526 -2.8535 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8478 -1.2039 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7306 -2.0867 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.5410 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 5.7345 -0.0702 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 9 1 0 0 0 0 2 13 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 13 2 0 0 0 0 10 16 2 0 0 0 0 10 19 1 0 0 0 0 11 17 2 0 0 0 0 11 18 1 0 0 0 0 12 35 1 0 0 0 0 12 36 1 0 0 0 0 13 28 1 0 0 0 0 14 3 1 6 0 0 0 14 15 1 0 0 0 0 14 22 1 0 0 0 0 15 4 1 6 0 0 0 15 23 1 0 0 0 0 16 20 1 0 0 0 0 16 22 1 0 0 0 0 17 21 1 0 0 0 0 17 23 1 0 0 0 0 18 24 2 0 0 0 0 18 31 1 0 0 0 0 19 25 2 0 0 0 0 19 35 1 0 0 0 0 20 21 1 0 0 0 0 20 27 2 0 0 0 0 21 26 2 0 0 0 0 22 29 1 6 0 0 0 23 37 1 1 0 0 0 24 26 1 0 0 0 0 24 32 1 0 0 0 0 25 27 1 0 0 0 0 25 36 1 0 0 0 0 26 33 1 0 0 0 0 27 34 1 0 0 0 0 28 30 2 0 0 0 0 28 37 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	514.22
Volume:	516.639
LogP:	3.462
LogD:	3.204
LogS:	-4.319
# Rotatable Bonds:	7
TPSA:	101.91
# H-Bond Aceptor:	9
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.422
Synthetic Accessibility Score:	4.262
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:	-4.756
MDCK Permeability:	2.6814135708264075e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.037

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.068
Plasma Protein Binding (PPB):	76.9651107788086%
Volume Distribution (VD):	1.048
Pgp-substrate:	12.949524879455566%

ADMET: Metabolism

CYP1A2-inhibitor:	0.069
CYP1A2-substrate:	0.983
CYP2C19-inhibitor:	0.959
CYP2C19-substrate:	0.93
CYP2C9-inhibitor:	0.913
CYP2C9-substrate:	0.873
CYP2D6-inhibitor:	0.252
CYP2D6-substrate:	0.502
CYP3A4-inhibitor:	0.937
CYP3A4-substrate:	0.914

ADMET: Excretion

Clearance (CL):	3.815
Half-life (T1/2):	0.167

ADMET: Toxicity

hERG Blockers:	0.191
Human Hepatotoxicity (H-HT):	0.069
Drug-inuced Liver Injury (DILI):	0.585
AMES Toxicity:	0.032
Rat Oral Acute Toxicity:	0.029
Maximum Recommended Daily Dose:	0.032
Skin Sensitization:	0.045
Carcinogencity:	0.041
Eye Corrosion:	0.003
Eye Irritation:	0.066
Respiratory Toxicity:	0.186

Download Data

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

Natural Product: NPC24562

Natural Product ID:	NPC24562
*Common Name:**	Ananosin A
IUPAC Name:	n.a.
Synonyms:	Ananosin A
Standard InCHIKey:	YREZDJJVCCDBTG-INQFUDPWSA-N
Standard InCHI:	InChI=1S/C28H34O9/c1-9-13(2)28(30)37-23-15(4)14(3)22(29)16-10-19-25(36-12-35-19)27(34-8)20(16)21-17(23)11-18(31-5)24(32-6)26(21)33-7/h9-11,14-15,22-23,29H,12H2,1-8H3/b13-9+/t14-,15+,22-,23-/m1/s1
SMILES:	C/C=C(C)/C(=O)O[C@@H]1[C@@H](C)[C@@H](C)[C@H](c2cc3c(c(c2-c2c1cc(c(c2OC)OC)OC)OC)OCO3)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1782123
PubChem CID:	636622
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
NPO27599	Kadsura ananosma	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15165154]
NPO27599	Kadsura ananosma	Species	Schisandraceae	Eukaryota	Stems	n.a.	n.a.	PMID[20025236]
NPO27599	Kadsura ananosma	Species	Schisandraceae	Eukaryota	n.a.	seed	n.a.	PMID[21381710]
NPO27599	Kadsura ananosma	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27599	Kadsura ananosma	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	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT519	Cell Line	SH-SY5Y	Homo sapiens	Activity	=	66.4	%	PMID[460976]
NPT519	Cell Line	SH-SY5Y	Homo sapiens	Activity	=	68.2	%	PMID[460976]

☑ 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 NPC24562 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	321
0.1-0.2	1343
0.2-0.3	3353
0.3-0.4	7773
0.4-0.5	10571
0.5-0.6	4236
0.6-0.7	7248
0.7-0.8	7009
0.8-0.85	647
0.85-0.9	121
0.9-0.95	51
0.95-1	24

Similarity Score	Similarity Level	Natural Product ID
0.9797	High Similarity	NPC473323
0.9796	High Similarity	NPC312763
0.973	High Similarity	NPC476065
0.9728	High Similarity	NPC77237
0.9728	High Similarity	NPC53669
0.9728	High Similarity	NPC217708
0.9728	High Similarity	NPC16791
0.9728	High Similarity	NPC308739
0.9728	High Similarity	NPC126405
0.9728	High Similarity	NPC297271
0.9655	High Similarity	NPC327352
0.9655	High Similarity	NPC325720
0.9655	High Similarity	NPC316676
0.9655	High Similarity	NPC252281
0.9655	High Similarity	NPC477375
0.9655	High Similarity	NPC198129
0.96	High Similarity	NPC475592
0.9592	High Similarity	NPC224472
0.9589	High Similarity	NPC322426
0.9589	High Similarity	NPC477374
0.9589	High Similarity	NPC477376
0.953	High Similarity	NPC198461
0.953	High Similarity	NPC473425
0.9527	High Similarity	NPC471154
0.9524	High Similarity	NPC316989
0.9524	High Similarity	NPC473989
0.9463	High Similarity	NPC474606
0.9459	High Similarity	NPC475756
0.9456	High Similarity	NPC85141
0.9448	High Similarity	NPC318286
0.9448	High Similarity	NPC327651
0.9408	High Similarity	NPC215400
0.9408	High Similarity	NPC230531
0.9392	High Similarity	NPC477381
0.9384	High Similarity	NPC321958
0.9384	High Similarity	NPC321696
0.9379	High Similarity	NPC326144
0.9338	High Similarity	NPC238834
0.9333	High Similarity	NPC477377
0.9329	High Similarity	NPC477379
0.9324	High Similarity	NPC474347
0.9324	High Similarity	NPC474393
0.932	High Similarity	NPC295297
0.931	High Similarity	NPC218510
0.931	High Similarity	NPC324962
0.931	High Similarity	NPC76415
0.9267	High Similarity	NPC475229
0.9267	High Similarity	NPC477378
0.9262	High Similarity	NPC470916
0.9241	High Similarity	NPC36531
0.9241	High Similarity	NPC230538
0.9241	High Similarity	NPC103637
0.9241	High Similarity	NPC229172
0.9205	High Similarity	NPC149735
0.9184	High Similarity	NPC475868
0.915	High Similarity	NPC29727
0.915	High Similarity	NPC477380
0.9145	High Similarity	NPC348849
0.9145	High Similarity	NPC178195
0.9128	High Similarity	NPC477879
0.9122	High Similarity	NPC474054
0.9116	High Similarity	NPC172171
0.9116	High Similarity	NPC239254
0.9097	High Similarity	NPC63061
0.9091	High Similarity	NPC477885
0.906	High Similarity	NPC183083
0.906	High Similarity	NPC137352
0.9054	High Similarity	NPC197352
0.9054	High Similarity	NPC166506
0.9054	High Similarity	NPC110763
0.9054	High Similarity	NPC189239
0.9051	High Similarity	NPC83049
0.9051	High Similarity	NPC118162
0.9051	High Similarity	NPC320471
0.9	High Similarity	NPC304821
0.8994	High Similarity	NPC311912
0.8986	High Similarity	NPC87883
0.8986	High Similarity	NPC121661
0.8986	High Similarity	NPC73467
0.898	High Similarity	NPC287124
0.8966	High Similarity	NPC865
0.8954	High Similarity	NPC475141
0.8947	High Similarity	NPC303519
0.8938	High Similarity	NPC88557
0.8924	High Similarity	NPC469475
0.8924	High Similarity	NPC475865
0.8924	High Similarity	NPC469518
0.8917	High Similarity	NPC319749
0.891	High Similarity	NPC325122
0.8904	High Similarity	NPC290714
0.8904	High Similarity	NPC201404
0.8904	High Similarity	NPC53722
0.8896	High Similarity	NPC473736
0.8882	High Similarity	NPC24425
0.8882	High Similarity	NPC477883
0.8875	High Similarity	NPC79322
0.8875	High Similarity	NPC471180
0.8867	High Similarity	NPC154971
0.8867	High Similarity	NPC252286
0.8867	High Similarity	NPC212890
0.8859	High Similarity	NPC141569
0.8859	High Similarity	NPC166884
0.8859	High Similarity	NPC477701
0.8854	High Similarity	NPC474770
0.8851	High Similarity	NPC133934
0.8851	High Similarity	NPC184641
0.8851	High Similarity	NPC184684
0.8846	High Similarity	NPC207584
0.8846	High Similarity	NPC19947
0.8831	High Similarity	NPC245948
0.88	High Similarity	NPC477702
0.8797	High Similarity	NPC191352
0.8797	High Similarity	NPC258322
0.879	High Similarity	NPC173726
0.879	High Similarity	NPC241600
0.8782	High Similarity	NPC237946
0.8782	High Similarity	NPC32373
0.8773	High Similarity	NPC477881
0.8767	High Similarity	NPC143895
0.8766	High Similarity	NPC302610
0.8759	High Similarity	NPC256776
0.8759	High Similarity	NPC145722
0.8759	High Similarity	NPC185680
0.875	High Similarity	NPC477884
0.8742	High Similarity	NPC469512
0.8742	High Similarity	NPC280778
0.8742	High Similarity	NPC249070
0.8718	High Similarity	NPC117154
0.8712	High Similarity	NPC471181
0.871	High Similarity	NPC474514
0.8699	High Similarity	NPC236522
0.8679	High Similarity	NPC288149
0.8649	High Similarity	NPC471183
0.8645	High Similarity	NPC56184
0.8639	High Similarity	NPC32189
0.8639	High Similarity	NPC11453
0.8627	High Similarity	NPC252402
0.8627	High Similarity	NPC93924
0.8627	High Similarity	NPC102934
0.8625	High Similarity	NPC42797
0.8625	High Similarity	NPC473445
0.8616	High Similarity	NPC119910
0.8616	High Similarity	NPC268718
0.8616	High Similarity	NPC96593
0.8616	High Similarity	NPC150943
0.8616	High Similarity	NPC91634
0.8614	High Similarity	NPC477882
0.8614	High Similarity	NPC477880
0.8609	High Similarity	NPC473046
0.8609	High Similarity	NPC472712
0.8609	High Similarity	NPC472713
0.8609	High Similarity	NPC187774
0.8609	High Similarity	NPC118385
0.8609	High Similarity	NPC297342
0.8598	High Similarity	NPC469506
0.8598	High Similarity	NPC178737
0.8591	High Similarity	NPC103448
0.8591	High Similarity	NPC46591
0.8591	High Similarity	NPC216434
0.8581	High Similarity	NPC474039
0.8581	High Similarity	NPC3072
0.8581	High Similarity	NPC477700
0.8581	High Similarity	NPC156948
0.8581	High Similarity	NPC283949
0.8581	High Similarity	NPC301765
0.8581	High Similarity	NPC32079
0.8581	High Similarity	NPC86605
0.8581	High Similarity	NPC46277
0.8571	High Similarity	NPC477698
0.8571	High Similarity	NPC291977
0.8571	High Similarity	NPC150534
0.8571	High Similarity	NPC283839
0.8571	High Similarity	NPC106138
0.8571	High Similarity	NPC90896
0.8562	High Similarity	NPC196937
0.8562	High Similarity	NPC100465
0.8562	High Similarity	NPC58585
0.8562	High Similarity	NPC152424
0.8552	High Similarity	NPC184928
0.8552	High Similarity	NPC141493
0.8544	High Similarity	NPC469474
0.8544	High Similarity	NPC228357
0.8543	High Similarity	NPC474808
0.8535	High Similarity	NPC136757
0.8526	High Similarity	NPC220577
0.8526	High Similarity	NPC478268
0.8519	High Similarity	NPC222531
0.8516	High Similarity	NPC185955
0.8516	High Similarity	NPC218041
0.8516	High Similarity	NPC9933
0.8516	High Similarity	NPC472710
0.8516	High Similarity	NPC260781
0.8516	High Similarity	NPC145979
0.8516	High Similarity	NPC469707
0.8516	High Similarity	NPC469706
0.8516	High Similarity	NPC182368
0.8516	High Similarity	NPC472709
0.8516	High Similarity	NPC214326
0.8516	High Similarity	NPC225815
0.8514	High Similarity	NPC197166

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 NPC24562 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	875
0.2-0.3	1801
0.3-0.4	2714
0.4-0.5	1822
0.5-0.6	978
0.6-0.7	556
0.7-0.8	119
0.8-0.85	4
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8831	High Similarity	NPD37	Approved
0.8782	High Similarity	NPD4965	Approved
0.8782	High Similarity	NPD4967	Phase 2
0.8782	High Similarity	NPD4966	Approved
0.8553	High Similarity	NPD6234	Discontinued
0.8415	Intermediate Similarity	NPD7228	Approved
0.8333	Intermediate Similarity	NPD7199	Phase 2
0.8121	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.8107	Intermediate Similarity	NPD7240	Approved
0.8101	Intermediate Similarity	NPD1653	Approved
0.7976	Intermediate Similarity	NPD3818	Discontinued
0.7929	Intermediate Similarity	NPD5844	Phase 1
0.7925	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7922	Intermediate Similarity	NPD7266	Discontinued
0.7919	Intermediate Similarity	NPD3027	Phase 3
0.7862	Intermediate Similarity	NPD3705	Approved
0.7848	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7811	Intermediate Similarity	NPD7473	Discontinued
0.7778	Intermediate Similarity	NPD7074	Phase 3
0.7758	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7738	Intermediate Similarity	NPD6232	Discontinued
0.7719	Intermediate Similarity	NPD7054	Approved
0.7714	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7707	Intermediate Similarity	NPD6674	Discontinued
0.7688	Intermediate Similarity	NPD6559	Discontinued
0.7674	Intermediate Similarity	NPD7472	Approved
0.7647	Intermediate Similarity	NPD1613	Approved
0.7647	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD1465	Phase 2
0.7557	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7543	Intermediate Similarity	NPD7808	Phase 3
0.7543	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7541	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD7819	Suspended
0.75	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD7251	Discontinued
0.7486	Intermediate Similarity	NPD7685	Pre-registration
0.7485	Intermediate Similarity	NPD3817	Phase 2
0.7471	Intermediate Similarity	NPD8127	Discontinued
0.747	Intermediate Similarity	NPD1934	Approved
0.744	Intermediate Similarity	NPD3882	Suspended
0.7434	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.743	Intermediate Similarity	NPD6843	Phase 3
0.743	Intermediate Similarity	NPD6842	Approved
0.743	Intermediate Similarity	NPD6841	Approved
0.7429	Intermediate Similarity	NPD6797	Phase 2
0.7421	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD4060	Phase 1
0.7412	Intermediate Similarity	NPD5494	Approved
0.7403	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.738	Intermediate Similarity	NPD7680	Approved
0.7362	Intermediate Similarity	NPD2533	Approved
0.7362	Intermediate Similarity	NPD2534	Approved
0.7362	Intermediate Similarity	NPD2532	Approved
0.7358	Intermediate Similarity	NPD5763	Approved
0.7358	Intermediate Similarity	NPD5762	Approved
0.7341	Intermediate Similarity	NPD6166	Phase 2
0.7341	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7341	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD3750	Approved
0.7326	Intermediate Similarity	NPD7229	Phase 3
0.7321	Intermediate Similarity	NPD8455	Phase 2
0.7321	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD3018	Phase 2
0.7317	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD1357	Approved
0.7294	Intermediate Similarity	NPD7075	Discontinued
0.7273	Intermediate Similarity	NPD4908	Phase 1
0.7261	Intermediate Similarity	NPD6355	Discontinued
0.7261	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD5124	Phase 1
0.7257	Intermediate Similarity	NPD3751	Discontinued
0.7255	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7247	Intermediate Similarity	NPD7549	Discontinued
0.7246	Intermediate Similarity	NPD4380	Phase 2
0.7222	Intermediate Similarity	NPD4628	Phase 3
0.7219	Intermediate Similarity	NPD2801	Approved
0.7219	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD8313	Approved
0.7207	Intermediate Similarity	NPD8312	Approved
0.7195	Intermediate Similarity	NPD4357	Discontinued
0.7179	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD6190	Approved
0.7176	Intermediate Similarity	NPD5402	Approved
0.7171	Intermediate Similarity	NPD2983	Phase 2
0.7171	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD2982	Phase 2
0.716	Intermediate Similarity	NPD6801	Discontinued
0.716	Intermediate Similarity	NPD1652	Phase 2
0.7152	Intermediate Similarity	NPD1091	Approved
0.7152	Intermediate Similarity	NPD230	Phase 1
0.7152	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD1610	Phase 2
0.7152	Intermediate Similarity	NPD422	Phase 1
0.7151	Intermediate Similarity	NPD919	Approved
0.7135	Intermediate Similarity	NPD7768	Phase 2
0.7133	Intermediate Similarity	NPD4626	Approved
0.7126	Intermediate Similarity	NPD3787	Discontinued
0.7125	Intermediate Similarity	NPD3748	Approved
0.7123	Intermediate Similarity	NPD5283	Phase 1
0.7117	Intermediate Similarity	NPD4110	Phase 3
0.7117	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD4625	Phase 3
0.7105	Intermediate Similarity	NPD2981	Phase 2
0.7098	Intermediate Similarity	NPD8151	Discontinued
0.7097	Intermediate Similarity	NPD2861	Phase 2
0.7091	Intermediate Similarity	NPD6799	Approved
0.7089	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD3620	Phase 2
0.7088	Intermediate Similarity	NPD8434	Phase 2
0.7086	Intermediate Similarity	NPD3926	Phase 2
0.7083	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD7458	Discontinued
0.7081	Intermediate Similarity	NPD2935	Discontinued
0.7081	Intermediate Similarity	NPD2438	Suspended
0.7076	Intermediate Similarity	NPD5353	Approved
0.7076	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD6959	Discontinued
0.7067	Intermediate Similarity	NPD5691	Approved
0.7066	Intermediate Similarity	NPD5403	Approved
0.7063	Intermediate Similarity	NPD7097	Phase 1
0.7047	Intermediate Similarity	NPD5536	Phase 2
0.7041	Intermediate Similarity	NPD7028	Phase 2
0.7041	Intermediate Similarity	NPD6599	Discontinued
0.7018	Intermediate Similarity	NPD5563	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5090	Approved
0.7	Intermediate Similarity	NPD6653	Approved
0.7	Intermediate Similarity	NPD7411	Suspended
0.7	Intermediate Similarity	NPD5089	Approved
0.6994	Remote Similarity	NPD3749	Approved
0.6989	Remote Similarity	NPD5242	Approved
0.6988	Remote Similarity	NPD1511	Approved
0.6982	Remote Similarity	NPD4005	Discontinued
0.6982	Remote Similarity	NPD6055	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD4140	Approved
0.6977	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD6099	Approved
0.6975	Remote Similarity	NPD6100	Approved
0.6968	Remote Similarity	NPD2797	Approved
0.6963	Remote Similarity	NPD5005	Approved
0.6963	Remote Similarity	NPD5006	Approved
0.6951	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD4749	Approved
0.6946	Remote Similarity	NPD5401	Approved
0.6937	Remote Similarity	NPD1933	Approved
0.6937	Remote Similarity	NPD447	Suspended
0.6933	Remote Similarity	NPD6004	Phase 3
0.6933	Remote Similarity	NPD6002	Phase 3
0.6933	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD6005	Phase 3
0.6933	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD7033	Discontinued
0.6914	Remote Similarity	NPD1510	Phase 2
0.6909	Remote Similarity	NPD3892	Phase 2
0.6905	Remote Similarity	NPD1512	Approved
0.6905	Remote Similarity	NPD6273	Approved
0.6903	Remote Similarity	NPD1283	Approved
0.6899	Remote Similarity	NPD7095	Approved
0.689	Remote Similarity	NPD1549	Phase 2
0.6887	Remote Similarity	NPD1548	Phase 1
0.6875	Remote Similarity	NPD1240	Approved
0.6875	Remote Similarity	NPD2979	Phase 3
0.6875	Remote Similarity	NPD1247	Approved
0.6871	Remote Similarity	NPD2796	Approved
0.6871	Remote Similarity	NPD1551	Phase 2
0.6867	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD3496	Discontinued
0.6855	Remote Similarity	NPD6798	Discontinued
0.6855	Remote Similarity	NPD3268	Approved
0.6855	Remote Similarity	NPD3764	Approved
0.6854	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD7296	Approved
0.6842	Remote Similarity	NPD4420	Approved
0.6839	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD7435	Discontinued
0.6836	Remote Similarity	NPD5710	Approved
0.6836	Remote Similarity	NPD5711	Approved
0.6829	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD3540	Phase 1
0.6826	Remote Similarity	NPD6666	Approved
0.6826	Remote Similarity	NPD6667	Approved
0.6826	Remote Similarity	NPD5058	Phase 3
0.6824	Remote Similarity	NPD3686	Approved
0.6824	Remote Similarity	NPD3687	Approved
0.6821	Remote Similarity	NPD2978	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