NPASS Compound

Structure

NPC471601 OpenBabel07101718202D 38 43 0 0 1 0 0 0 0 0999 V2000 1.0285 1.5896 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5785 4.0782 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7754 -4.1823 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7981 -4.1823 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6831 2.4117 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8536 2.9283 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4404 -0.8928 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0550 -2.8473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2989 -2.2742 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5940 -3.3360 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1331 -1.8701 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2867 -1.3814 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7477 -2.8473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4653 0.6947 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7477 0.0845 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9719 -1.6834 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4886 0.7274 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.0386 3.2160 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5940 -0.4041 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9820 1.5242 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.4404 -2.8473 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 1.9014 -0.4041 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1331 -2.8473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3975 -0.8928 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5940 -1.3814 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 3.9587 1.4916 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.2867 -3.3360 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8209 1.9516 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4404 -1.8701 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.7477 -1.8701 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.9014 -1.3814 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9719 -0.1022 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.0153 3.1833 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4404 0.0845 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9794 -3.3360 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5219 2.3864 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 4.7882 0.9749 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 18 1 0 0 0 0 3 27 1 0 0 0 0 4 27 1 0 0 0 0 5 28 1 0 0 0 0 6 28 1 0 0 0 0 8 30 1 0 0 0 0 10 13 1 0 0 0 0 10 21 1 0 0 0 0 11 12 1 0 0 0 0 11 23 1 0 0 0 0 12 29 1 0 0 0 0 13 30 1 0 0 0 0 14 17 1 0 0 0 0 15 19 1 0 0 0 0 15 22 2 0 0 0 0 16 24 1 0 0 0 0 16 31 1 0 0 0 0 17 1 1 6 0 0 0 18 33 2 0 0 0 0 18 36 1 0 0 0 0 19 25 1 0 0 0 0 19 34 2 0 0 0 0 20 14 1 6 0 0 0 20 36 1 0 0 0 0 21 27 1 0 0 0 0 21 29 1 0 0 0 0 22 31 1 0 0 0 0 22 32 1 0 0 0 0 23 27 1 0 0 0 0 23 35 2 0 0 0 0 24 32 1 1 0 0 0 24 37 1 0 0 0 0 25 29 1 0 0 0 0 25 30 1 0 0 0 0 26 20 1 6 0 0 0 26 28 1 0 0 0 0 26 38 1 0 0 0 0 28 38 1 0 0 0 0 29 7 1 6 0 0 0 30 31 1 6 0 0 0 31 9 1 6 0 0 0 32 17 1 1 0 0 0 32 37 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	526.33
Volume:	552.885
LogP:	4.56
LogD:	3.765
LogS:	-5.212
# Rotatable Bonds:	6
TPSA:	85.5
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	6
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.342
Synthetic Accessibility Score:	5.543
Fsp3:	0.844
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:	-5.151
MDCK Permeability:	1.88167341548251e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.018
20% Bioavailability (F20%):	0.993
30% Bioavailability (F30%):	0.981

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.709
Plasma Protein Binding (PPB):	86.11087799072266%
Volume Distribution (VD):	1.833
Pgp-substrate:	13.011273384094238%

ADMET: Metabolism

CYP1A2-inhibitor:	0.004
CYP1A2-substrate:	0.741
CYP2C19-inhibitor:	0.133
CYP2C19-substrate:	0.931
CYP2C9-inhibitor:	0.256
CYP2C9-substrate:	0.021
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.104
CYP3A4-inhibitor:	0.799
CYP3A4-substrate:	0.878

ADMET: Excretion

Clearance (CL):	5.792
Half-life (T1/2):	0.198

ADMET: Toxicity

hERG Blockers:	0.269
Human Hepatotoxicity (H-HT):	0.485
Drug-inuced Liver Injury (DILI):	0.195
AMES Toxicity:	0.022
Rat Oral Acute Toxicity:	0.746
Maximum Recommended Daily Dose:	0.916
Skin Sensitization:	0.247
Carcinogencity:	0.578
Eye Corrosion:	0.011
Eye Irritation:	0.015
Respiratory Toxicity:	0.985

Download Data

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

Natural Product: NPC471601

Natural Product ID:	NPC471601
*Common Name:**	UUJREHQYYSZHDT-LQUTUFCSSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	UUJREHQYYSZHDT-LQUTUFCSSA-N
Standard InCHI:	InChI=1S/C32H46O6/c1-17(14-20(36-18(2)33)26-28(5,6)38-26)32-22-15-19(34)25-29(7)12-11-23(35)27(3,4)21(29)10-13-30(25,8)31(22,9)16-24(32)37-32/h15,17,20-21,24-26H,10-14,16H2,1-9H3/t17-,20+,21?,24+,25?,26-,29+,30+,31+,32-/m1/s1
SMILES:	CC(CC(C1C(O1)(C)C)OC(=O)C)C23C(O2)CC4(C3=CC(=O)C5C4(CCC6C5(CCC(=O)C6(C)C)C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL274783
PubChem CID:	44268629
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO30648	Alisma orientale	Species	Alismataceae	Eukaryota	rhizome	n.a.	n.a.	PMID[10560729]
NPO30648	Alisma orientale	Species	Alismataceae	Eukaryota	n.a.	rhizome	n.a.	PMID[17541191]
NPO30648	Alisma orientale	Species	Alismataceae	Eukaryota	Rhizome	n.a.	n.a.	PMID[26425784]
NPO30648	Alisma orientale	Species	Alismataceae	Eukaryota	n.a.	tuber	n.a.	PMID[26666273]
NPO30648	Alisma orientale	Species	Alismataceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]

☑ 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
Organism	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	9.9	%	PMID[455171]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	11.9	%	PMID[455171]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	31.1	%	PMID[455171]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	83.6	%	PMID[455171]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	113.6	%	PMID[455171]
NPT32	Organism	Mus musculus	Mus musculus	IC50	>	10000.0	nM	PMID[455171]

☑ 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 NPC471601 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	271
0.1-0.2	1589
0.2-0.3	5297
0.3-0.4	11329
0.4-0.5	10110
0.5-0.6	7055
0.6-0.7	5828
0.7-0.8	1164
0.8-0.85	53
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8378	Intermediate Similarity	NPC268213
0.8276	Intermediate Similarity	NPC8374
0.8257	Intermediate Similarity	NPC253906
0.8173	Intermediate Similarity	NPC176845
0.8148	Intermediate Similarity	NPC180744
0.8113	Intermediate Similarity	NPC22388
0.8103	Intermediate Similarity	NPC88326
0.8103	Intermediate Similarity	NPC153700
0.8095	Intermediate Similarity	NPC167974
0.8091	Intermediate Similarity	NPC472215
0.8091	Intermediate Similarity	NPC472214
0.8077	Intermediate Similarity	NPC151488
0.807	Intermediate Similarity	NPC153440
0.8053	Intermediate Similarity	NPC190286
0.8017	Intermediate Similarity	NPC67569
0.8017	Intermediate Similarity	NPC204731
0.8	Intermediate Similarity	NPC5292
0.8	Intermediate Similarity	NPC270850
0.8	Intermediate Similarity	NPC475041
0.8	Intermediate Similarity	NPC173905
0.8	Intermediate Similarity	NPC305260
0.8	Intermediate Similarity	NPC284828
0.8	Intermediate Similarity	NPC469370
0.8	Intermediate Similarity	NPC475520
0.8	Intermediate Similarity	NPC299590
0.8	Intermediate Similarity	NPC472216
0.8	Intermediate Similarity	NPC5475
0.8	Intermediate Similarity	NPC222303
0.7983	Intermediate Similarity	NPC287423
0.7966	Intermediate Similarity	NPC469790
0.7963	Intermediate Similarity	NPC169843
0.7949	Intermediate Similarity	NPC470265
0.7949	Intermediate Similarity	NPC23786
0.7946	Intermediate Similarity	NPC236217
0.7946	Intermediate Similarity	NPC471933
0.7944	Intermediate Similarity	NPC475320
0.7934	Intermediate Similarity	NPC241935
0.7934	Intermediate Similarity	NPC279478
0.7931	Intermediate Similarity	NPC474370
0.7931	Intermediate Similarity	NPC79579
0.7931	Intermediate Similarity	NPC474585
0.7913	Intermediate Similarity	NPC473720
0.7909	Intermediate Similarity	NPC472825
0.7909	Intermediate Similarity	NPC470269
0.7909	Intermediate Similarity	NPC61411
0.7905	Intermediate Similarity	NPC100912
0.7899	Intermediate Similarity	NPC15095
0.7899	Intermediate Similarity	NPC473635
0.7895	Intermediate Similarity	NPC148458
0.7895	Intermediate Similarity	NPC470793
0.789	Intermediate Similarity	NPC469874
0.789	Intermediate Similarity	NPC470975
0.789	Intermediate Similarity	NPC470979
0.789	Intermediate Similarity	NPC103088
0.7885	Intermediate Similarity	NPC33473
0.7885	Intermediate Similarity	NPC281134
0.7881	Intermediate Similarity	NPC469789
0.7881	Intermediate Similarity	NPC6193
0.7876	Intermediate Similarity	NPC33360
0.7876	Intermediate Similarity	NPC317210
0.7869	Intermediate Similarity	NPC34963
0.7863	Intermediate Similarity	NPC46570
0.7863	Intermediate Similarity	NPC310511
0.7857	Intermediate Similarity	NPC469656
0.7857	Intermediate Similarity	NPC474846
0.7857	Intermediate Similarity	NPC469655
0.7851	Intermediate Similarity	NPC35109
0.7845	Intermediate Similarity	NPC264954
0.7838	Intermediate Similarity	NPC471934
0.7833	Intermediate Similarity	NPC42399
0.783	Intermediate Similarity	NPC107806
0.783	Intermediate Similarity	NPC72647
0.783	Intermediate Similarity	NPC471582
0.7826	Intermediate Similarity	NPC239273
0.7826	Intermediate Similarity	NPC58662
0.7805	Intermediate Similarity	NPC58029
0.7805	Intermediate Similarity	NPC469673
0.78	Intermediate Similarity	NPC195640
0.78	Intermediate Similarity	NPC474045
0.78	Intermediate Similarity	NPC261253
0.7798	Intermediate Similarity	NPC164835
0.7798	Intermediate Similarity	NPC146731
0.7798	Intermediate Similarity	NPC228669
0.7797	Intermediate Similarity	NPC170538
0.7797	Intermediate Similarity	NPC269642
0.7797	Intermediate Similarity	NPC107493
0.7788	Intermediate Similarity	NPC477093
0.7788	Intermediate Similarity	NPC42658
0.7788	Intermediate Similarity	NPC470063
0.7788	Intermediate Similarity	NPC191620
0.7788	Intermediate Similarity	NPC222834
0.7788	Intermediate Similarity	NPC473522
0.7788	Intermediate Similarity	NPC150228
0.7788	Intermediate Similarity	NPC475524
0.7788	Intermediate Similarity	NPC475277
0.7788	Intermediate Similarity	NPC214005
0.7788	Intermediate Similarity	NPC100267
0.7788	Intermediate Similarity	NPC269530
0.7787	Intermediate Similarity	NPC220757
0.7787	Intermediate Similarity	NPC196921
0.7778	Intermediate Similarity	NPC473928
0.7778	Intermediate Similarity	NPC271266
0.7778	Intermediate Similarity	NPC308351
0.7768	Intermediate Similarity	NPC469917
0.7768	Intermediate Similarity	NPC472417
0.7767	Intermediate Similarity	NPC221282
0.7759	Intermediate Similarity	NPC288679
0.7759	Intermediate Similarity	NPC50774
0.7759	Intermediate Similarity	NPC709
0.7759	Intermediate Similarity	NPC470420
0.775	Intermediate Similarity	NPC293112
0.7748	Intermediate Similarity	NPC472217
0.7748	Intermediate Similarity	NPC469916
0.7748	Intermediate Similarity	NPC472439
0.7748	Intermediate Similarity	NPC472218
0.7748	Intermediate Similarity	NPC472219
0.7745	Intermediate Similarity	NPC177141
0.7742	Intermediate Similarity	NPC476823
0.7739	Intermediate Similarity	NPC176840
0.7739	Intermediate Similarity	NPC243981
0.7736	Intermediate Similarity	NPC311241
0.7736	Intermediate Similarity	NPC38530
0.7736	Intermediate Similarity	NPC475446
0.7736	Intermediate Similarity	NPC110937
0.7736	Intermediate Similarity	NPC84335
0.7731	Intermediate Similarity	NPC473979
0.7731	Intermediate Similarity	NPC204812
0.7731	Intermediate Similarity	NPC11895
0.7719	Intermediate Similarity	NPC250109
0.7719	Intermediate Similarity	NPC962
0.7719	Intermediate Similarity	NPC159333
0.7706	Intermediate Similarity	NPC165608
0.7706	Intermediate Similarity	NPC254202
0.7705	Intermediate Similarity	NPC471407
0.77	Intermediate Similarity	NPC323765
0.7699	Intermediate Similarity	NPC317107
0.7699	Intermediate Similarity	NPC231589
0.7699	Intermediate Similarity	NPC118860
0.7699	Intermediate Similarity	NPC324683
0.7699	Intermediate Similarity	NPC214797
0.7699	Intermediate Similarity	NPC475495
0.7692	Intermediate Similarity	NPC472667
0.7692	Intermediate Similarity	NPC475657
0.7685	Intermediate Similarity	NPC99411
0.7685	Intermediate Similarity	NPC310981
0.7679	Intermediate Similarity	NPC241927
0.7679	Intermediate Similarity	NPC258543
0.7672	Intermediate Similarity	NPC470492
0.7672	Intermediate Similarity	NPC140055
0.7672	Intermediate Similarity	NPC167606
0.7672	Intermediate Similarity	NPC286528
0.7672	Intermediate Similarity	NPC20302
0.7667	Intermediate Similarity	NPC172154
0.7667	Intermediate Similarity	NPC241456
0.7667	Intermediate Similarity	NPC81736
0.7667	Intermediate Similarity	NPC32868
0.7667	Intermediate Similarity	NPC8369
0.7664	Intermediate Similarity	NPC153792
0.7664	Intermediate Similarity	NPC271387
0.7664	Intermediate Similarity	NPC98868
0.7664	Intermediate Similarity	NPC264378
0.7658	Intermediate Similarity	NPC475294
0.7658	Intermediate Similarity	NPC469318
0.7658	Intermediate Similarity	NPC144459
0.7658	Intermediate Similarity	NPC67321
0.7658	Intermediate Similarity	NPC187435
0.7658	Intermediate Similarity	NPC473173
0.7652	Intermediate Similarity	NPC474181
0.7652	Intermediate Similarity	NPC43213
0.7647	Intermediate Similarity	NPC470612
0.7647	Intermediate Similarity	NPC470613
0.7642	Intermediate Similarity	NPC173347
0.7642	Intermediate Similarity	NPC471170
0.7642	Intermediate Similarity	NPC471775
0.7642	Intermediate Similarity	NPC475380
0.7642	Intermediate Similarity	NPC42042
0.7642	Intermediate Similarity	NPC209297
0.7642	Intermediate Similarity	NPC111684
0.7642	Intermediate Similarity	NPC194132
0.7642	Intermediate Similarity	NPC322063
0.7642	Intermediate Similarity	NPC58052
0.7636	Intermediate Similarity	NPC296950
0.7636	Intermediate Similarity	NPC119493
0.7636	Intermediate Similarity	NPC477127
0.7636	Intermediate Similarity	NPC473543
0.7636	Intermediate Similarity	NPC473175
0.7632	Intermediate Similarity	NPC221144
0.7632	Intermediate Similarity	NPC126691
0.7632	Intermediate Similarity	NPC152117
0.7632	Intermediate Similarity	NPC476163
0.7632	Intermediate Similarity	NPC234042
0.7632	Intermediate Similarity	NPC241477
0.7632	Intermediate Similarity	NPC170487
0.7632	Intermediate Similarity	NPC317687
0.7627	Intermediate Similarity	NPC268530
0.7627	Intermediate Similarity	NPC251226
0.7627	Intermediate Similarity	NPC154491
0.7627	Intermediate Similarity	NPC4548
0.7624	Intermediate Similarity	NPC286153
0.7624	Intermediate Similarity	NPC220478

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 NPC471601 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	229
0.1-0.2	1848
0.2-0.3	4010
0.3-0.4	2064
0.4-0.5	553
0.5-0.6	212
0.6-0.7	187
0.7-0.8	45
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8148	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.8056	Intermediate Similarity	NPD6008	Approved
0.8	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7928	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.78	Intermediate Similarity	NPD6684	Approved
0.78	Intermediate Similarity	NPD7334	Approved
0.78	Intermediate Similarity	NPD7146	Approved
0.78	Intermediate Similarity	NPD7521	Approved
0.78	Intermediate Similarity	NPD6409	Approved
0.78	Intermediate Similarity	NPD5330	Approved
0.7767	Intermediate Similarity	NPD5693	Phase 1
0.7672	Intermediate Similarity	NPD7115	Discovery
0.7647	Intermediate Similarity	NPD6903	Approved
0.7647	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7573	Intermediate Similarity	NPD6673	Approved
0.7573	Intermediate Similarity	NPD6080	Approved
0.7573	Intermediate Similarity	NPD6904	Approved
0.757	Intermediate Similarity	NPD6083	Phase 2
0.757	Intermediate Similarity	NPD6084	Phase 2
0.7547	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7638	Approved
0.75	Intermediate Similarity	NPD6412	Phase 2
0.7478	Intermediate Similarity	NPD6053	Discontinued
0.7478	Intermediate Similarity	NPD8297	Approved
0.7476	Intermediate Similarity	NPD5737	Approved
0.7476	Intermediate Similarity	NPD6672	Approved
0.7434	Intermediate Similarity	NPD6686	Approved
0.7431	Intermediate Similarity	NPD7640	Approved
0.7431	Intermediate Similarity	NPD7639	Approved
0.7411	Intermediate Similarity	NPD6675	Approved
0.7411	Intermediate Similarity	NPD7128	Approved
0.7411	Intermediate Similarity	NPD6402	Approved
0.7411	Intermediate Similarity	NPD5739	Approved
0.7404	Intermediate Similarity	NPD6051	Approved
0.7383	Intermediate Similarity	NPD5695	Phase 3
0.7358	Intermediate Similarity	NPD6399	Phase 3
0.7339	Intermediate Similarity	NPD5696	Approved
0.7317	Intermediate Similarity	NPD7507	Approved
0.7308	Intermediate Similarity	NPD5208	Approved
0.7304	Intermediate Similarity	NPD6371	Approved
0.729	Intermediate Similarity	NPD6001	Approved
0.7282	Intermediate Similarity	NPD6098	Approved
0.7281	Intermediate Similarity	NPD7320	Approved
0.7281	Intermediate Similarity	NPD6899	Approved
0.7281	Intermediate Similarity	NPD6881	Approved
0.7265	Intermediate Similarity	NPD4632	Approved
0.7264	Intermediate Similarity	NPD6050	Approved
0.7241	Intermediate Similarity	NPD8130	Phase 1
0.7228	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7217	Intermediate Similarity	NPD6372	Approved
0.7217	Intermediate Similarity	NPD6373	Approved
0.7193	Intermediate Similarity	NPD5697	Approved
0.7193	Intermediate Similarity	NPD5701	Approved
0.719	Intermediate Similarity	NPD6319	Approved
0.717	Intermediate Similarity	NPD46	Approved
0.717	Intermediate Similarity	NPD5692	Phase 3
0.717	Intermediate Similarity	NPD6698	Approved
0.7155	Intermediate Similarity	NPD7290	Approved
0.7155	Intermediate Similarity	NPD6883	Approved
0.7155	Intermediate Similarity	NPD7102	Approved
0.7154	Intermediate Similarity	NPD7604	Phase 2
0.7143	Intermediate Similarity	NPD7319	Approved
0.7131	Intermediate Similarity	NPD8033	Approved
0.713	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD7900	Approved
0.712	Intermediate Similarity	NPD8293	Discontinued
0.7103	Intermediate Similarity	NPD5694	Approved
0.7097	Intermediate Similarity	NPD7492	Approved
0.7094	Intermediate Similarity	NPD6650	Approved
0.7094	Intermediate Similarity	NPD6847	Approved
0.7094	Intermediate Similarity	NPD6869	Approved
0.7094	Intermediate Similarity	NPD6649	Approved
0.7094	Intermediate Similarity	NPD6617	Approved
0.7083	Intermediate Similarity	NPD6009	Approved
0.7075	Intermediate Similarity	NPD4753	Phase 2
0.7069	Intermediate Similarity	NPD6012	Approved
0.7069	Intermediate Similarity	NPD6014	Approved
0.7069	Intermediate Similarity	NPD6013	Approved
0.7063	Intermediate Similarity	NPD7736	Approved
0.7049	Intermediate Similarity	NPD8377	Approved
0.7049	Intermediate Similarity	NPD6054	Approved
0.7049	Intermediate Similarity	NPD8294	Approved
0.7049	Intermediate Similarity	NPD6059	Approved
0.704	Intermediate Similarity	NPD6616	Approved
0.7034	Intermediate Similarity	NPD6882	Approved
0.7025	Intermediate Similarity	NPD7328	Approved
0.7025	Intermediate Similarity	NPD7327	Approved
0.7019	Intermediate Similarity	NPD1694	Approved
0.7009	Intermediate Similarity	NPD5207	Approved
0.6992	Remote Similarity	NPD7503	Approved
0.6992	Remote Similarity	NPD5983	Phase 2
0.6992	Remote Similarity	NPD8296	Approved
0.6992	Remote Similarity	NPD8380	Approved
0.6992	Remote Similarity	NPD8379	Approved
0.6992	Remote Similarity	NPD8335	Approved
0.6992	Remote Similarity	NPD8378	Approved
0.6991	Remote Similarity	NPD7632	Discontinued
0.6984	Remote Similarity	NPD7078	Approved
0.6983	Remote Similarity	NPD6011	Approved
0.6975	Remote Similarity	NPD8133	Approved
0.6972	Remote Similarity	NPD7748	Approved
0.6967	Remote Similarity	NPD7516	Approved
0.6964	Remote Similarity	NPD6648	Approved
0.6949	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD5281	Approved
0.6944	Remote Similarity	NPD5284	Approved
0.6937	Remote Similarity	NPD7902	Approved
0.6937	Remote Similarity	NPD4755	Approved
0.6937	Remote Similarity	NPD5959	Approved
0.6935	Remote Similarity	NPD6370	Approved
0.6923	Remote Similarity	NPD3665	Phase 1
0.6923	Remote Similarity	NPD3133	Approved
0.6923	Remote Similarity	NPD3666	Approved
0.6916	Remote Similarity	NPD1695	Approved
0.6909	Remote Similarity	NPD5654	Approved
0.6905	Remote Similarity	NPD6336	Discontinued
0.6903	Remote Similarity	NPD5344	Discontinued
0.6897	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD4223	Phase 3
0.6893	Remote Similarity	NPD4221	Approved
0.6881	Remote Similarity	NPD4202	Approved
0.6857	Remote Similarity	NPD5329	Approved
0.6855	Remote Similarity	NPD6016	Approved
0.6855	Remote Similarity	NPD6015	Approved
0.6842	Remote Similarity	NPD5211	Phase 2
0.6814	Remote Similarity	NPD5285	Approved
0.6814	Remote Similarity	NPD5286	Approved
0.6814	Remote Similarity	NPD4700	Approved
0.6814	Remote Similarity	NPD4696	Approved
0.68	Remote Similarity	NPD5988	Approved
0.6783	Remote Similarity	NPD6052	Approved
0.6762	Remote Similarity	NPD4786	Approved
0.6762	Remote Similarity	NPD4197	Approved
0.6757	Remote Similarity	NPD5210	Approved
0.6757	Remote Similarity	NPD4629	Approved
0.6726	Remote Similarity	NPD4225	Approved
0.6724	Remote Similarity	NPD5141	Approved
0.6723	Remote Similarity	NPD4634	Approved
0.6721	Remote Similarity	NPD6274	Approved
0.6698	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD7838	Discovery
0.6696	Remote Similarity	NPD5225	Approved
0.6696	Remote Similarity	NPD5224	Approved
0.6696	Remote Similarity	NPD5226	Approved
0.6696	Remote Similarity	NPD4633	Approved
0.6695	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD7100	Approved
0.6694	Remote Similarity	NPD7101	Approved
0.6639	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6638	Remote Similarity	NPD5174	Approved
0.6638	Remote Similarity	NPD5175	Approved
0.6636	Remote Similarity	NPD4689	Approved
0.6636	Remote Similarity	NPD7515	Phase 2
0.6636	Remote Similarity	NPD4138	Approved
0.6636	Remote Similarity	NPD4693	Phase 3
0.6636	Remote Similarity	NPD4688	Approved
0.6636	Remote Similarity	NPD4690	Approved
0.6636	Remote Similarity	NPD5205	Approved
0.6613	Remote Similarity	NPD6335	Approved
0.661	Remote Similarity	NPD6614	Approved
0.6609	Remote Similarity	NPD5223	Approved
0.6606	Remote Similarity	NPD5328	Approved
0.6604	Remote Similarity	NPD3668	Phase 3
0.6587	Remote Similarity	NPD6908	Approved
0.6587	Remote Similarity	NPD6909	Approved
0.6574	Remote Similarity	NPD3573	Approved
0.6571	Remote Similarity	NPD3667	Approved
0.6545	Remote Similarity	NPD5785	Approved
0.6538	Remote Similarity	NPD6033	Approved
0.6532	Remote Similarity	NPD6317	Approved
0.6525	Remote Similarity	NPD4768	Approved
0.6525	Remote Similarity	NPD4767	Approved
0.6515	Remote Similarity	NPD7260	Phase 2
0.6496	Remote Similarity	NPD4754	Approved
0.6486	Remote Similarity	NPD8034	Phase 2
0.6486	Remote Similarity	NPD8035	Phase 2
0.6486	Remote Similarity	NPD7637	Suspended
0.6486	Remote Similarity	NPD6079	Approved
0.6484	Remote Similarity	NPD8328	Phase 3
0.6484	Remote Similarity	NPD6067	Discontinued
0.6481	Remote Similarity	NPD5280	Approved
0.6481	Remote Similarity	NPD5690	Phase 2
0.6481	Remote Similarity	NPD4694	Approved
0.6481	Remote Similarity	NPD3618	Phase 1
0.6481	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.648	Remote Similarity	NPD6314	Approved
0.648	Remote Similarity	NPD6313	Approved
0.6455	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6439	Remote Similarity	NPD5956	Approved
0.6417	Remote Similarity	NPD5128	Approved
0.6417	Remote Similarity	NPD4729	Approved
0.6417	Remote Similarity	NPD4730	Approved
0.6404	Remote Similarity	NPD7732	Phase 3
0.64	Remote Similarity	NPD5777	Approved
0.6393	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD8039	Approved
0.6355	Remote Similarity	NPD4788	Approved
0.6343	Remote Similarity	NPD6845	Suspended
0.633	Remote Similarity	NPD4519	Discontinued
0.633	Remote Similarity	NPD5279	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