NPASS Compound

Structure

CID10945 OpenBabel06191715342D 33 37 0 0 1 0 0 0 0 0999 V2000 0.8783 -0.5071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3897 -0.0004 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3892 -2.9354 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5422 0.4890 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5419 -2.4466 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8476 -1.4681 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.9787 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2370 -1.4679 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.9561 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3897 -0.9791 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2367 -2.4461 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5422 -1.4684 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6946 -0.9790 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6946 -0.0003 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8470 0.4890 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8470 1.4670 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.1688 1.2047 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.0667 0.2323 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3777 1.7792 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.1736 -0.1654 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8476 0.4894 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.0716 -1.1378 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4846 1.3814 0.0000 C 0 0 2 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 -5.1150 -2.9533 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0619 1.6025 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8577 -0.3422 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4798 2.7516 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7137 -0.0104 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1785 -1.5355 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8626 -1.7123 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6936 1.9560 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3826 0.4091 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 4 1 0 0 0 0 2 10 1 0 0 0 0 3 5 1 0 0 0 0 3 11 2 0 0 0 0 5 12 2 0 0 0 0 6 7 1 0 0 0 0 7 24 1 0 0 0 0 8 10 2 0 0 0 0 8 11 1 0 0 0 0 9 15 1 0 0 0 0 9 16 1 0 0 0 0 10 12 1 0 0 0 0 11 25 1 0 0 0 0 12 13 1 0 0 0 0 13 6 1 6 0 0 0 13 14 1 0 0 0 0 14 4 1 1 0 0 0 14 15 1 0 0 0 0 15 24 1 6 0 0 0 16 21 1 0 0 0 0 16 32 1 1 0 0 0 17 18 1 0 0 0 0 17 19 1 0 0 0 0 17 26 1 1 0 0 0 18 20 1 0 0 0 0 18 27 1 6 0 0 0 19 23 1 0 0 0 0 19 28 1 6 0 0 0 20 22 1 1 0 0 0 20 33 1 0 0 0 0 21 24 1 6 0 0 0 21 29 1 0 0 0 0 22 30 2 0 0 0 0 22 31 1 0 0 0 0 23 32 1 1 0 0 0 23 33 1 0 0 0 0 24 1 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	464.2
Volume:	449.444
LogP:	1.82
LogD:	1.39
LogS:	-3.104
# Rotatable Bonds:	3
TPSA:	156.91
# H-Bond Aceptor:	9
# H-Bond Donor:	6
# Rings:	5
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.375
Synthetic Accessibility Score:	4.662
Fsp3:	0.708
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:	-6.314
MDCK Permeability:	1.6341578884748742e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.979
Human Intestinal Absorption (HIA):	0.958
20% Bioavailability (F20%):	0.06
30% Bioavailability (F30%):	0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.07
Plasma Protein Binding (PPB):	84.49787902832031%
Volume Distribution (VD):	0.33
Pgp-substrate:	8.179529190063477%

ADMET: Metabolism

CYP1A2-inhibitor:	0.018
CYP1A2-substrate:	0.063
CYP2C19-inhibitor:	0.019
CYP2C19-substrate:	0.094
CYP2C9-inhibitor:	0.002
CYP2C9-substrate:	0.846
CYP2D6-inhibitor:	0.016
CYP2D6-substrate:	0.15
CYP3A4-inhibitor:	0.016
CYP3A4-substrate:	0.027

ADMET: Excretion

Clearance (CL):	1.575
Half-life (T1/2):	0.873

ADMET: Toxicity

hERG Blockers:	0.199
Human Hepatotoxicity (H-HT):	0.31
Drug-inuced Liver Injury (DILI):	0.152
AMES Toxicity:	0.04
Rat Oral Acute Toxicity:	0.157
Maximum Recommended Daily Dose:	0.075
Skin Sensitization:	0.702
Carcinogencity:	0.23
Eye Corrosion:	0.003
Eye Irritation:	0.014
Respiratory Toxicity:	0.67

Download Data

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

Natural Product: NPC10945

Natural Product ID:	NPC10945
*Common Name:**	Estriol-16-Glucuronide
IUPAC Name:	(2S,3S,4S,5R,6R)-6-[[(8R,9S,13S,14S,16R,17R)-3,17-dihydroxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-16-yl]oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
Synonyms:
Standard InCHIKey:	FQYGGFDZJFIDPU-JRSYHJKYSA-N
Standard InCHI:	InChI=1S/C24H32O9/c1-24-7-6-13-12-5-3-11(25)8-10(12)2-4-14(13)15(24)9-16(21(24)29)32-23-19(28)17(26)18(27)20(33-23)22(30)31/h3,5,8,13-21,23,25-29H,2,4,6-7,9H2,1H3,(H,30,31)/t13-,14-,15+,16-,17+,18+,19-,20+,21+,23-,24+/m1/s1
SMILES:	C[C@]12CC[C@@H]3c4ccc(cc4CC[C@H]3[C@@H]1C[C@H]([C@@H]2O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](C(=O)O)O1)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2074802
PubChem CID:	122281
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001013] Steroidal glycosides

*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

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
Others	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT957	Individual Protein	Multidrug resistance-associated protein 7	Homo sapiens	Activity	=	53.0	%	PMID[548216]

☑ 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 NPC10945 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	334
0.1-0.2	1195
0.2-0.3	2807
0.3-0.4	4969
0.4-0.5	9545
0.5-0.6	11736
0.6-0.7	9888
0.7-0.8	2179
0.8-0.85	39
0.85-0.9	1
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9299	High Similarity	NPC318472
0.9236	High Similarity	NPC327694
0.8931	High Similarity	NPC326278
0.8418	Intermediate Similarity	NPC77310
0.8408	Intermediate Similarity	NPC96599
0.8402	Intermediate Similarity	NPC475613
0.8397	Intermediate Similarity	NPC470330
0.8344	Intermediate Similarity	NPC208676
0.8344	Intermediate Similarity	NPC130489
0.8323	Intermediate Similarity	NPC475484
0.8313	Intermediate Similarity	NPC469419
0.8284	Intermediate Similarity	NPC195972
0.8261	Intermediate Similarity	NPC209393
0.8261	Intermediate Similarity	NPC205172
0.8247	Intermediate Similarity	NPC3218
0.8239	Intermediate Similarity	NPC240592
0.8239	Intermediate Similarity	NPC117346
0.8228	Intermediate Similarity	NPC95990
0.821	Intermediate Similarity	NPC3449
0.8205	Intermediate Similarity	NPC96447
0.8193	Intermediate Similarity	NPC471861
0.8187	Intermediate Similarity	NPC475407
0.8182	Intermediate Similarity	NPC477627
0.8171	Intermediate Similarity	NPC314795
0.816	Intermediate Similarity	NPC148323
0.816	Intermediate Similarity	NPC475378
0.816	Intermediate Similarity	NPC283480
0.8141	Intermediate Similarity	NPC204644
0.8133	Intermediate Similarity	NPC471850
0.8117	Intermediate Similarity	NPC324262
0.8117	Intermediate Similarity	NPC62800
0.8114	Intermediate Similarity	NPC299855
0.8114	Intermediate Similarity	NPC96194
0.811	Intermediate Similarity	NPC206641
0.811	Intermediate Similarity	NPC208651
0.8101	Intermediate Similarity	NPC320734
0.8098	Intermediate Similarity	NPC82190
0.8098	Intermediate Similarity	NPC174599
0.8098	Intermediate Similarity	NPC192219
0.809	Intermediate Similarity	NPC475299
0.8089	Intermediate Similarity	NPC251062
0.8089	Intermediate Similarity	NPC202391
0.8089	Intermediate Similarity	NPC296659
0.8089	Intermediate Similarity	NPC184464
0.8086	Intermediate Similarity	NPC257847
0.8084	Intermediate Similarity	NPC161151
0.8077	Intermediate Similarity	NPC2681
0.8077	Intermediate Similarity	NPC272907
0.8075	Intermediate Similarity	NPC475379
0.8072	Intermediate Similarity	NPC471858
0.807	Intermediate Similarity	NPC471871
0.807	Intermediate Similarity	NPC124828
0.8068	Intermediate Similarity	NPC189704
0.8063	Intermediate Similarity	NPC473719
0.8035	Intermediate Similarity	NPC469418
0.8025	Intermediate Similarity	NPC186296
0.8024	Intermediate Similarity	NPC145847
0.8023	Intermediate Similarity	NPC476067
0.8023	Intermediate Similarity	NPC475121
0.8013	Intermediate Similarity	NPC476407
0.8012	Intermediate Similarity	NPC179128
0.8012	Intermediate Similarity	NPC267469
0.8012	Intermediate Similarity	NPC116292
0.8012	Intermediate Similarity	NPC35097
0.8012	Intermediate Similarity	NPC269668
0.8012	Intermediate Similarity	NPC87630
0.8	Intermediate Similarity	NPC120728
0.8	Intermediate Similarity	NPC469549
0.8	Intermediate Similarity	NPC471870
0.7988	Intermediate Similarity	NPC88176
0.7988	Intermediate Similarity	NPC469458
0.7988	Intermediate Similarity	NPC474501
0.7988	Intermediate Similarity	NPC149002
0.7988	Intermediate Similarity	NPC469396
0.7988	Intermediate Similarity	NPC38699
0.7987	Intermediate Similarity	NPC212808
0.7976	Intermediate Similarity	NPC109990
0.7975	Intermediate Similarity	NPC194938
0.7975	Intermediate Similarity	NPC477207
0.7963	Intermediate Similarity	NPC158546
0.7963	Intermediate Similarity	NPC289021
0.7961	Intermediate Similarity	NPC471095
0.7961	Intermediate Similarity	NPC471066
0.7952	Intermediate Similarity	NPC53139
0.7952	Intermediate Similarity	NPC179914
0.795	Intermediate Similarity	NPC94781
0.795	Intermediate Similarity	NPC477206
0.7949	Intermediate Similarity	NPC164743
0.7947	Intermediate Similarity	NPC470122
0.7947	Intermediate Similarity	NPC469705
0.7947	Intermediate Similarity	NPC17968
0.7941	Intermediate Similarity	NPC471860
0.7941	Intermediate Similarity	NPC471859
0.7935	Intermediate Similarity	NPC310252
0.7935	Intermediate Similarity	NPC302583
0.7935	Intermediate Similarity	NPC100558
0.7935	Intermediate Similarity	NPC84789
0.7929	Intermediate Similarity	NPC329647
0.7929	Intermediate Similarity	NPC470735
0.7925	Intermediate Similarity	NPC126707
0.7917	Intermediate Similarity	NPC187934
0.7917	Intermediate Similarity	NPC97637
0.7914	Intermediate Similarity	NPC205918
0.7908	Intermediate Similarity	NPC164172
0.7907	Intermediate Similarity	NPC222665
0.7907	Intermediate Similarity	NPC271755
0.7907	Intermediate Similarity	NPC183441
0.7907	Intermediate Similarity	NPC254071
0.7907	Intermediate Similarity	NPC149502
0.7901	Intermediate Similarity	NPC162569
0.7901	Intermediate Similarity	NPC12006
0.7901	Intermediate Similarity	NPC44378
0.7901	Intermediate Similarity	NPC35160
0.7901	Intermediate Similarity	NPC280753
0.7898	Intermediate Similarity	NPC7518
0.7898	Intermediate Similarity	NPC154262
0.7898	Intermediate Similarity	NPC137501
0.7898	Intermediate Similarity	NPC159387
0.7892	Intermediate Similarity	NPC187205
0.7882	Intermediate Similarity	NPC469459
0.7877	Intermediate Similarity	NPC71385
0.7877	Intermediate Similarity	NPC230670
0.7875	Intermediate Similarity	NPC208293
0.7875	Intermediate Similarity	NPC119773
0.7875	Intermediate Similarity	NPC475539
0.7875	Intermediate Similarity	NPC143246
0.7875	Intermediate Similarity	NPC474268
0.7867	Intermediate Similarity	NPC30491
0.7867	Intermediate Similarity	NPC262936
0.7866	Intermediate Similarity	NPC229354
0.7862	Intermediate Similarity	NPC63304
0.7853	Intermediate Similarity	NPC69425
0.784	Intermediate Similarity	NPC329657
0.7836	Intermediate Similarity	NPC286809
0.7833	Intermediate Similarity	NPC112708
0.7831	Intermediate Similarity	NPC163635
0.7829	Intermediate Similarity	NPC260300
0.7826	Intermediate Similarity	NPC474991
0.7816	Intermediate Similarity	NPC475244
0.7815	Intermediate Similarity	NPC158673
0.7812	Intermediate Similarity	NPC475528
0.7811	Intermediate Similarity	NPC471873
0.7806	Intermediate Similarity	NPC158325
0.7806	Intermediate Similarity	NPC180171
0.7806	Intermediate Similarity	NPC103398
0.7806	Intermediate Similarity	NPC123988
0.7805	Intermediate Similarity	NPC478235
0.7803	Intermediate Similarity	NPC477617
0.7803	Intermediate Similarity	NPC13989
0.7803	Intermediate Similarity	NPC148185
0.7798	Intermediate Similarity	NPC295408
0.7798	Intermediate Similarity	NPC150893
0.7798	Intermediate Similarity	NPC329960
0.7797	Intermediate Similarity	NPC473776
0.7797	Intermediate Similarity	NPC473205
0.7792	Intermediate Similarity	NPC49742
0.7791	Intermediate Similarity	NPC476017
0.7791	Intermediate Similarity	NPC21956
0.7791	Intermediate Similarity	NPC120171
0.779	Intermediate Similarity	NPC473711
0.7784	Intermediate Similarity	NPC257309
0.7784	Intermediate Similarity	NPC29552
0.7778	Intermediate Similarity	NPC28776
0.7778	Intermediate Similarity	NPC473138
0.7778	Intermediate Similarity	NPC127046
0.7771	Intermediate Similarity	NPC220936
0.7771	Intermediate Similarity	NPC31745
0.7771	Intermediate Similarity	NPC176246
0.7765	Intermediate Similarity	NPC25889
0.7765	Intermediate Similarity	NPC116759
0.7765	Intermediate Similarity	NPC14294
0.7765	Intermediate Similarity	NPC100420
0.7764	Intermediate Similarity	NPC170055
0.7764	Intermediate Similarity	NPC473147
0.7758	Intermediate Similarity	NPC471874
0.7758	Intermediate Similarity	NPC299706
0.7758	Intermediate Similarity	NPC61604
0.7758	Intermediate Similarity	NPC115466
0.7758	Intermediate Similarity	NPC87403
0.7758	Intermediate Similarity	NPC245615
0.7758	Intermediate Similarity	NPC154675
0.7751	Intermediate Similarity	NPC117943
0.7751	Intermediate Similarity	NPC471869
0.7751	Intermediate Similarity	NPC293568
0.7751	Intermediate Similarity	NPC152424
0.7751	Intermediate Similarity	NPC100465
0.775	Intermediate Similarity	NPC100242
0.7746	Intermediate Similarity	NPC475058
0.7746	Intermediate Similarity	NPC478021
0.7742	Intermediate Similarity	NPC169398
0.774	Intermediate Similarity	NPC102367
0.7738	Intermediate Similarity	NPC469654
0.7736	Intermediate Similarity	NPC296643
0.7736	Intermediate Similarity	NPC477595
0.7733	Intermediate Similarity	NPC185498
0.773	Intermediate Similarity	NPC478234
0.773	Intermediate Similarity	NPC161955
0.773	Intermediate Similarity	NPC478236
0.7727	Intermediate Similarity	NPC159811
0.7727	Intermediate Similarity	NPC80360

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 NPC10945 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	274
0.1-0.2	761
0.2-0.3	1685
0.3-0.4	2858
0.4-0.5	2129
0.5-0.6	1086
0.6-0.7	307
0.7-0.8	50
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8108	Intermediate Similarity	NPD5736	Approved
0.8013	Intermediate Similarity	NPD6663	Approved
0.7852	Intermediate Similarity	NPD3094	Phase 2
0.7733	Intermediate Similarity	NPD7799	Discontinued
0.7733	Intermediate Similarity	NPD7228	Approved
0.7703	Intermediate Similarity	NPD3092	Approved
0.7667	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7657	Intermediate Similarity	NPD7685	Pre-registration
0.7584	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD7266	Discontinued
0.7545	Intermediate Similarity	NPD37	Approved
0.7529	Intermediate Similarity	NPD6234	Discontinued
0.7515	Intermediate Similarity	NPD4967	Phase 2
0.7515	Intermediate Similarity	NPD4966	Approved
0.7515	Intermediate Similarity	NPD4965	Approved
0.7469	Intermediate Similarity	NPD6190	Approved
0.7457	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD5763	Approved
0.7438	Intermediate Similarity	NPD5762	Approved
0.7432	Intermediate Similarity	NPD3091	Approved
0.7374	Intermediate Similarity	NPD8313	Approved
0.7374	Intermediate Similarity	NPD8312	Approved
0.736	Intermediate Similarity	NPD7240	Approved
0.7341	Intermediate Similarity	NPD7199	Phase 2
0.7333	Intermediate Similarity	NPD3019	Approved
0.7316	Intermediate Similarity	NPD8319	Approved
0.7316	Intermediate Similarity	NPD8320	Phase 1
0.7288	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD4140	Approved
0.7263	Intermediate Similarity	NPD7435	Discontinued
0.7253	Intermediate Similarity	NPD8150	Discontinued
0.7233	Intermediate Similarity	NPD5735	Approved
0.7229	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD3095	Discontinued
0.7219	Intermediate Similarity	NPD2932	Approved
0.7212	Intermediate Similarity	NPD7236	Approved
0.72	Intermediate Similarity	NPD3787	Discontinued
0.7195	Intermediate Similarity	NPD8166	Discontinued
0.7193	Intermediate Similarity	NPD8455	Phase 2
0.7186	Intermediate Similarity	NPD6273	Approved
0.717	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD7251	Discontinued
0.7143	Intermediate Similarity	NPD8127	Discontinued
0.7127	Intermediate Similarity	NPD7808	Phase 3
0.7112	Intermediate Similarity	NPD6534	Approved
0.7112	Intermediate Similarity	NPD6535	Approved
0.7111	Intermediate Similarity	NPD6797	Phase 2
0.7101	Intermediate Similarity	NPD7239	Suspended
0.709	Intermediate Similarity	NPD7700	Phase 2
0.709	Intermediate Similarity	NPD7699	Phase 2
0.7069	Intermediate Similarity	NPD7075	Discontinued
0.7069	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD3620	Phase 2
0.7063	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD7074	Phase 3
0.7048	Intermediate Similarity	NPD7910	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD7874	Approved
0.7041	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD3751	Discontinued
0.703	Intermediate Similarity	NPD6674	Discontinued
0.7019	Intermediate Similarity	NPD6355	Discontinued
0.7016	Intermediate Similarity	NPD6780	Approved
0.7016	Intermediate Similarity	NPD6778	Approved
0.7016	Intermediate Similarity	NPD6776	Approved
0.7016	Intermediate Similarity	NPD6782	Approved
0.7016	Intermediate Similarity	NPD6777	Approved
0.7016	Intermediate Similarity	NPD6779	Approved
0.7016	Intermediate Similarity	NPD6781	Approved
0.7	Intermediate Similarity	NPD7054	Approved
0.6989	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD4628	Phase 3
0.6983	Remote Similarity	NPD7473	Discontinued
0.6981	Remote Similarity	NPD7095	Approved
0.6978	Remote Similarity	NPD6559	Discontinued
0.6975	Remote Similarity	NPD6653	Approved
0.6973	Remote Similarity	NPD8434	Phase 2
0.6964	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD7472	Approved
0.6959	Remote Similarity	NPD7458	Discontinued
0.6957	Remote Similarity	NPD4060	Phase 1
0.6948	Remote Similarity	NPD3023	Approved
0.6948	Remote Similarity	NPD3026	Approved
0.6944	Remote Similarity	NPD3818	Discontinued
0.6933	Remote Similarity	NPD7097	Phase 1
0.6933	Remote Similarity	NPD2629	Approved
0.6928	Remote Similarity	NPD3025	Approved
0.6928	Remote Similarity	NPD3024	Approved
0.6919	Remote Similarity	NPD7028	Phase 2
0.691	Remote Similarity	NPD6232	Discontinued
0.6907	Remote Similarity	NPD7680	Approved
0.6907	Remote Similarity	NPD7697	Approved
0.6907	Remote Similarity	NPD7696	Phase 3
0.6907	Remote Similarity	NPD7698	Approved
0.6897	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD8032	Phase 2
0.6883	Remote Similarity	NPD4059	Approved
0.6872	Remote Similarity	NPD7871	Phase 2
0.6872	Remote Similarity	NPD7870	Phase 2
0.6853	Remote Similarity	NPD7701	Phase 2
0.6834	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6834	Remote Similarity	NPD7801	Approved
0.6834	Remote Similarity	NPD7783	Phase 2
0.6833	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD6166	Phase 2
0.6824	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD4380	Phase 2
0.6818	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD8151	Discontinued
0.6815	Remote Similarity	NPD5327	Phase 3
0.6813	Remote Similarity	NPD5844	Phase 1
0.68	Remote Similarity	NPD5760	Phase 2
0.68	Remote Similarity	NPD5761	Phase 2
0.68	Remote Similarity	NPD7819	Suspended
0.6793	Remote Similarity	NPD8368	Discontinued
0.6792	Remote Similarity	NPD5647	Approved
0.679	Remote Similarity	NPD6233	Phase 2
0.6789	Remote Similarity	NPD6213	Phase 3
0.6789	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD6212	Phase 3
0.6788	Remote Similarity	NPD7033	Discontinued
0.6774	Remote Similarity	NPD5126	Approved
0.6774	Remote Similarity	NPD5125	Phase 3
0.6774	Remote Similarity	NPD8407	Phase 2
0.6774	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD5408	Approved
0.6747	Remote Similarity	NPD5405	Approved
0.6747	Remote Similarity	NPD5404	Approved
0.6747	Remote Similarity	NPD5406	Approved
0.6743	Remote Similarity	NPD6801	Discontinued
0.6733	Remote Similarity	NPD7930	Approved
0.6728	Remote Similarity	NPD3764	Approved
0.6728	Remote Similarity	NPD6798	Discontinued
0.6725	Remote Similarity	NPD2533	Approved
0.6725	Remote Similarity	NPD2534	Approved
0.6725	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6725	Remote Similarity	NPD2532	Approved
0.6724	Remote Similarity	NPD6599	Discontinued
0.6723	Remote Similarity	NPD7057	Phase 3
0.6723	Remote Similarity	NPD7058	Phase 2
0.6722	Remote Similarity	NPD7315	Approved
0.6721	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD6002	Phase 3
0.6707	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD6004	Phase 3
0.6707	Remote Similarity	NPD6005	Phase 3
0.6699	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD7743	Approved
0.6687	Remote Similarity	NPD7742	Approved
0.6686	Remote Similarity	NPD4110	Phase 3
0.6686	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD6823	Phase 2
0.6667	Remote Similarity	NPD7390	Discontinued
0.6667	Remote Similarity	NPD4198	Discontinued
0.6667	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5402	Approved
0.6667	Remote Similarity	NPD3817	Phase 2
0.6667	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6959	Discontinued
0.6667	Remote Similarity	NPD6353	Approved
0.665	Remote Similarity	NPD7497	Discontinued
0.6649	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD6100	Approved
0.6647	Remote Similarity	NPD6099	Approved
0.6647	Remote Similarity	NPD2438	Suspended
0.6635	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD8360	Approved
0.6632	Remote Similarity	NPD8361	Approved
0.6632	Remote Similarity	NPD8435	Approved
0.663	Remote Similarity	NPD7229	Phase 3
0.6627	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6613	Remote Similarity	NPD6764	Approved
0.6613	Remote Similarity	NPD6765	Approved
0.661	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD7305	Phase 1
0.6584	Remote Similarity	NPD4624	Approved
0.6583	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6583	Remote Similarity	NPD7999	Approved
0.6571	Remote Similarity	NPD3226	Approved
0.6568	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD7736	Approved
0.6562	Remote Similarity	NPD7296	Approved
0.6556	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6554	Remote Similarity	NPD1934	Approved
0.6552	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6548	Remote Similarity	NPD2493	Approved
0.6548	Remote Similarity	NPD2494	Approved
0.6543	Remote Similarity	NPD2861	Phase 2
0.6538	Remote Similarity	NPD7741	Discontinued
0.6536	Remote Similarity	NPD3882	Suspended
0.6533	Remote Similarity	NPD4582	Approved
0.6533	Remote Similarity	NPD4583	Approved
0.6532	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD8424	Clinical (unspecified phase)

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