NPASS Compound

Structure

NPC474483 OpenBabel07101719142D 36 40 0 0 1 0 0 0 0 0999 V2000 -2.0981 -2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.7078 -1.9067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.3769 -1.1636 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -3.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.7942 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.9282 -2.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.8988 -0.5055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -3.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.1556 0.1637 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.8769 -0.2976 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 25 1 0 0 0 0 2 25 1 0 0 0 0 4 5 1 0 0 0 0 5 17 1 0 0 0 0 6 8 1 0 0 0 0 6 18 1 0 0 0 0 7 9 1 0 0 0 0 7 13 2 0 0 0 0 8 26 1 0 0 0 0 9 33 1 0 0 0 0 10 14 1 0 0 0 0 10 15 1 0 0 0 0 11 27 1 0 0 0 0 12 4 1 6 0 0 0 12 14 1 0 0 0 0 12 23 1 0 0 0 0 13 15 1 0 0 0 0 13 22 1 0 0 0 0 14 26 1 6 0 0 0 15 34 1 0 0 0 0 16 11 1 6 0 0 0 16 19 1 0 0 0 0 16 35 1 0 0 0 0 17 25 1 0 0 0 0 17 26 1 6 0 0 0 18 25 1 0 0 0 0 18 36 1 6 0 0 0 19 20 1 0 0 0 0 19 28 1 1 0 0 0 20 21 1 0 0 0 0 20 29 1 6 0 0 0 21 24 1 0 0 0 0 21 30 1 1 0 0 0 22 31 2 0 0 0 0 22 33 1 0 0 0 0 23 32 1 0 0 0 0 23 34 1 0 0 0 0 24 35 1 0 0 0 0 24 36 1 6 0 0 0 26 3 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	512.26
Volume:	498.099
LogP:	2.153
LogD:	2.856
LogS:	-3.117
# Rotatable Bonds:	4
TPSA:	162.21
# H-Bond Aceptor:	10
# H-Bond Donor:	6
# Rings:	5
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.325
Synthetic Accessibility Score:	5.113
Fsp3:	0.846
Lipinski Rule-of-5:	Rejected
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:	-6.046
MDCK Permeability:	2.4611310436739586e-05
Pgp-inhibitor:	0.59
Pgp-substrate:	0.333
Human Intestinal Absorption (HIA):	0.889
20% Bioavailability (F20%):	0.058
30% Bioavailability (F30%):	0.941

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.069
Plasma Protein Binding (PPB):	90.61329650878906%
Volume Distribution (VD):	0.662
Pgp-substrate:	11.978242874145508%

ADMET: Metabolism

CYP1A2-inhibitor:	0.006
CYP1A2-substrate:	0.064
CYP2C19-inhibitor:	0.007
CYP2C19-substrate:	0.401
CYP2C9-inhibitor:	0.012
CYP2C9-substrate:	0.111
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.183
CYP3A4-inhibitor:	0.01
CYP3A4-substrate:	0.099

ADMET: Excretion

Clearance (CL):	1.961
Half-life (T1/2):	0.72

ADMET: Toxicity

hERG Blockers:	0.027
Human Hepatotoxicity (H-HT):	0.145
Drug-inuced Liver Injury (DILI):	0.03
AMES Toxicity:	0.074
Rat Oral Acute Toxicity:	0.387
Maximum Recommended Daily Dose:	0.886
Skin Sensitization:	0.812
Carcinogencity:	0.082
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.959

Download Data

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

Natural Product: NPC474483

Natural Product ID:	NPC474483
*Common Name:**	Curcumanggoside
IUPAC Name:	4-[(4aS,6aR,8S,10aR,10bS)-4-hydroxy-7,7,10a-trimethyl-8-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,4,4a,5,6,6a,8,9,10,10b-decahydro-1H-benzo[f]isochromen-2-yl]-2H-furan-5-one
Synonyms:	curcumanggoside
Standard InCHIKey:	FPNUJGSJUSZNKB-CUBBGWLLSA-N
Standard InCHI:	InChI=1S/C26H40O10/c1-25(2)17-5-4-12-14(10-15(34-23(12)32)13-7-9-33-22(13)31)26(17,3)8-6-18(25)36-24-21(30)20(29)19(28)16(11-27)35-24/h7,12,14-21,23-24,27-30,32H,4-6,8-11H2,1-3H3/t12-,14-,15?,16+,17-,18-,19+,20-,21+,23?,24-,26+/m0/s1
SMILES:	OC[C@H]1O[C@@H](O[C@H]2CC[C@]3([C@H](C2(C)C)CC[C@H]2[C@@H]3CC(OC2O)C2=CCOC2=O)C)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL469828
PubChem CID:	44559175
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides [CHEMONTID:0001755] Diterpene 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
NPO16667	Curcuma mangga	Species	Zingiberaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[16038556]
NPO16667	Curcuma mangga	Species	Zingiberaceae	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	1

Activity Type	# Activity
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	0.0	%	PMID[540222]

☑ 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 NPC474483 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	262
0.1-0.2	1530
0.2-0.3	4265
0.3-0.4	7151
0.4-0.5	12209
0.5-0.6	8172
0.6-0.7	5315
0.7-0.8	2717
0.8-0.85	759
0.85-0.9	288
0.9-0.95	24
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9727	High Similarity	NPC476127
0.9727	High Similarity	NPC476150
0.9464	High Similarity	NPC476204
0.9464	High Similarity	NPC170084
0.9252	High Similarity	NPC392
0.9252	High Similarity	NPC177524
0.9252	High Similarity	NPC219900
0.9204	High Similarity	NPC470312
0.9009	High Similarity	NPC264153
0.8991	High Similarity	NPC476759
0.8909	High Similarity	NPC476766
0.8898	High Similarity	NPC469757
0.8898	High Similarity	NPC146456
0.8898	High Similarity	NPC470516
0.8898	High Similarity	NPC117702
0.8898	High Similarity	NPC471357
0.887	High Similarity	NPC281840
0.885	High Similarity	NPC471816
0.885	High Similarity	NPC44170
0.8833	High Similarity	NPC311178
0.8833	High Similarity	NPC43589
0.8833	High Similarity	NPC300655
0.8833	High Similarity	NPC222951
0.8824	High Similarity	NPC472268
0.8824	High Similarity	NPC311534
0.8824	High Similarity	NPC472269
0.8824	High Similarity	NPC472270
0.8824	High Similarity	NPC23020
0.8824	High Similarity	NPC112492
0.8803	High Similarity	NPC27363
0.8785	High Similarity	NPC121423
0.8783	High Similarity	NPC122971
0.8772	High Similarity	NPC473405
0.8772	High Similarity	NPC473968
0.876	High Similarity	NPC322904
0.876	High Similarity	NPC233223
0.876	High Similarity	NPC475444
0.876	High Similarity	NPC183816
0.876	High Similarity	NPC324933
0.876	High Similarity	NPC319719
0.876	High Similarity	NPC196874
0.876	High Similarity	NPC475177
0.876	High Similarity	NPC473679
0.875	High Similarity	NPC477196
0.875	High Similarity	NPC469753
0.875	High Similarity	NPC469755
0.875	High Similarity	NPC471352
0.875	High Similarity	NPC197707
0.875	High Similarity	NPC70542
0.875	High Similarity	NPC469751
0.875	High Similarity	NPC10823
0.875	High Similarity	NPC471361
0.875	High Similarity	NPC251866
0.875	High Similarity	NPC80843
0.875	High Similarity	NPC89514
0.875	High Similarity	NPC180079
0.875	High Similarity	NPC17896
0.875	High Similarity	NPC9499
0.875	High Similarity	NPC1046
0.875	High Similarity	NPC284406
0.875	High Similarity	NPC469754
0.875	High Similarity	NPC471360
0.875	High Similarity	NPC471359
0.875	High Similarity	NPC219085
0.875	High Similarity	NPC6108
0.875	High Similarity	NPC476966
0.875	High Similarity	NPC471358
0.875	High Similarity	NPC86159
0.875	High Similarity	NPC469752
0.8739	High Similarity	NPC240070
0.8739	High Similarity	NPC329784
0.8739	High Similarity	NPC472666
0.8727	High Similarity	NPC476765
0.8716	High Similarity	NPC476760
0.8716	High Similarity	NPC476761
0.8716	High Similarity	NPC476762
0.8696	High Similarity	NPC471548
0.8696	High Similarity	NPC473617
0.8696	High Similarity	NPC239293
0.8696	High Similarity	NPC473828
0.8689	High Similarity	NPC116075
0.8689	High Similarity	NPC32793
0.8689	High Similarity	NPC469749
0.8689	High Similarity	NPC316915
0.8689	High Similarity	NPC247190
0.8689	High Similarity	NPC146857
0.8684	High Similarity	NPC268954
0.8678	High Similarity	NPC477197
0.8678	High Similarity	NPC25998
0.8678	High Similarity	NPC478155
0.8673	High Similarity	NPC238935
0.8673	High Similarity	NPC475208
0.8667	High Similarity	NPC220838
0.8667	High Similarity	NPC245094
0.8667	High Similarity	NPC477191
0.8667	High Similarity	NPC477194
0.8667	High Similarity	NPC477192
0.8667	High Similarity	NPC477193
0.8667	High Similarity	NPC45606
0.8661	High Similarity	NPC31839
0.8655	High Similarity	NPC250556
0.8655	High Similarity	NPC297950
0.8655	High Similarity	NPC469750
0.8649	High Similarity	NPC31522
0.8624	High Similarity	NPC476764
0.8624	High Similarity	NPC476763
0.8621	High Similarity	NPC476529
0.8621	High Similarity	NPC470914
0.8621	High Similarity	NPC475775
0.8618	High Similarity	NPC329636
0.8607	High Similarity	NPC476776
0.8607	High Similarity	NPC478153
0.8607	High Similarity	NPC477195
0.8607	High Similarity	NPC478152
0.8607	High Similarity	NPC478150
0.8607	High Similarity	NPC231240
0.8607	High Similarity	NPC478154
0.8596	High Similarity	NPC110861
0.8596	High Similarity	NPC475486
0.8596	High Similarity	NPC164389
0.8596	High Similarity	NPC472274
0.8595	High Similarity	NPC97918
0.8595	High Similarity	NPC47995
0.8595	High Similarity	NPC265841
0.8595	High Similarity	NPC88311
0.8595	High Similarity	NPC329986
0.8595	High Similarity	NPC115656
0.8595	High Similarity	NPC141600
0.8595	High Similarity	NPC470913
0.8595	High Similarity	NPC252657
0.8595	High Similarity	NPC276838
0.8595	High Similarity	NPC125077
0.8595	High Similarity	NPC11577
0.8595	High Similarity	NPC188234
0.8595	High Similarity	NPC305793
0.8595	High Similarity	NPC269484
0.8595	High Similarity	NPC477077
0.8595	High Similarity	NPC232785
0.8595	High Similarity	NPC280029
0.8595	High Similarity	NPC470518
0.8595	High Similarity	NPC140092
0.8595	High Similarity	NPC1314
0.8595	High Similarity	NPC472267
0.8595	High Similarity	NPC477076
0.8595	High Similarity	NPC273878
0.8595	High Similarity	NPC244296
0.8595	High Similarity	NPC252289
0.8595	High Similarity	NPC9470
0.8595	High Similarity	NPC107536
0.8595	High Similarity	NPC82380
0.8595	High Similarity	NPC477079
0.8584	High Similarity	NPC48249
0.8584	High Similarity	NPC471967
0.8583	High Similarity	NPC179412
0.8583	High Similarity	NPC470780
0.8583	High Similarity	NPC471356
0.8571	High Similarity	NPC164194
0.8571	High Similarity	NPC90856
0.8571	High Similarity	NPC127056
0.8571	High Similarity	NPC242611
0.8571	High Similarity	NPC475296
0.8571	High Similarity	NPC470922
0.8571	High Similarity	NPC56713
0.8571	High Similarity	NPC270667
0.8571	High Similarity	NPC59804
0.8571	High Similarity	NPC269095
0.8571	High Similarity	NPC318135
0.8571	High Similarity	NPC474589
0.8571	High Similarity	NPC78046
0.8571	High Similarity	NPC174679
0.8571	High Similarity	NPC136877
0.8571	High Similarity	NPC29069
0.8571	High Similarity	NPC279554
0.8559	High Similarity	NPC90946
0.8559	High Similarity	NPC473483
0.8559	High Similarity	NPC300614
0.8548	High Similarity	NPC194716
0.8547	High Similarity	NPC109607
0.8547	High Similarity	NPC473130
0.8547	High Similarity	NPC107338
0.8537	High Similarity	NPC476779
0.8537	High Similarity	NPC478151
0.8534	High Similarity	NPC470515
0.8534	High Similarity	NPC232237
0.8534	High Similarity	NPC105800
0.8532	High Similarity	NPC281378
0.8525	High Similarity	NPC173435
0.8525	High Similarity	NPC478065
0.8525	High Similarity	NPC264566
0.8525	High Similarity	NPC301639
0.8525	High Similarity	NPC16569
0.8525	High Similarity	NPC476074
0.8525	High Similarity	NPC478064
0.8525	High Similarity	NPC134914
0.8525	High Similarity	NPC262796
0.8525	High Similarity	NPC159338
0.8525	High Similarity	NPC172374
0.8525	High Similarity	NPC329993
0.8525	High Similarity	NPC476774
0.8525	High Similarity	NPC253456

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 NPC474483 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	232
0.1-0.2	1731
0.2-0.3	3623
0.3-0.4	2261
0.4-0.5	776
0.5-0.6	313
0.6-0.7	167
0.7-0.8	31
0.8-0.85	13
0.85-0.9	2
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9252	High Similarity	NPD6686	Approved
0.875	High Similarity	NPD7319	Approved
0.8655	High Similarity	NPD7507	Approved
0.839	Intermediate Similarity	NPD8377	Approved
0.839	Intermediate Similarity	NPD8294	Approved
0.8376	Intermediate Similarity	NPD7327	Approved
0.8376	Intermediate Similarity	NPD7328	Approved
0.8333	Intermediate Similarity	NPD8328	Phase 3
0.8319	Intermediate Similarity	NPD8380	Approved
0.8319	Intermediate Similarity	NPD8296	Approved
0.8319	Intermediate Similarity	NPD8379	Approved
0.8319	Intermediate Similarity	NPD8033	Approved
0.8319	Intermediate Similarity	NPD8335	Approved
0.8319	Intermediate Similarity	NPD8378	Approved
0.8305	Intermediate Similarity	NPD7516	Approved
0.819	Intermediate Similarity	NPD8133	Approved
0.8142	Intermediate Similarity	NPD6412	Phase 2
0.8017	Intermediate Similarity	NPD7503	Approved
0.8	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7983	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7869	Intermediate Similarity	NPD8513	Phase 3
0.7869	Intermediate Similarity	NPD8515	Approved
0.7869	Intermediate Similarity	NPD8517	Approved
0.7869	Intermediate Similarity	NPD8516	Approved
0.7845	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7838	Intermediate Similarity	NPD4225	Approved
0.7838	Intermediate Similarity	NPD7638	Approved
0.7833	Intermediate Similarity	NPD7115	Discovery
0.7778	Intermediate Similarity	NPD7736	Approved
0.7768	Intermediate Similarity	NPD7640	Approved
0.7768	Intermediate Similarity	NPD7639	Approved
0.7661	Intermediate Similarity	NPD6370	Approved
0.7627	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7559	Intermediate Similarity	NPD8293	Discontinued
0.754	Intermediate Similarity	NPD7492	Approved
0.75	Intermediate Similarity	NPD6054	Approved
0.75	Intermediate Similarity	NPD6319	Approved
0.748	Intermediate Similarity	NPD6616	Approved
0.7458	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7422	Intermediate Similarity	NPD7078	Approved
0.7373	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7364	Intermediate Similarity	NPD6698	Approved
0.7364	Intermediate Similarity	NPD46	Approved
0.736	Intermediate Similarity	NPD6059	Approved
0.7355	Intermediate Similarity	NPD6882	Approved
0.7302	Intermediate Similarity	NPD6016	Approved
0.7302	Intermediate Similarity	NPD6015	Approved
0.7273	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7258	Intermediate Similarity	NPD6009	Approved
0.7244	Intermediate Similarity	NPD5988	Approved
0.7213	Intermediate Similarity	NPD8297	Approved
0.7179	Intermediate Similarity	NPD7632	Discontinued
0.7168	Intermediate Similarity	NPD7748	Approved
0.7154	Intermediate Similarity	NPD4632	Approved
0.7154	Intermediate Similarity	NPD8074	Phase 3
0.7143	Intermediate Similarity	NPD7515	Phase 2
0.713	Intermediate Similarity	NPD7902	Approved
0.7103	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD6067	Discontinued
0.7049	Intermediate Similarity	NPD6371	Approved
0.7025	Intermediate Similarity	NPD6881	Approved
0.7025	Intermediate Similarity	NPD6899	Approved
0.7	Intermediate Similarity	NPD6402	Approved
0.7	Intermediate Similarity	NPD5739	Approved
0.7	Intermediate Similarity	NPD6675	Approved
0.7	Intermediate Similarity	NPD7128	Approved
0.6992	Remote Similarity	NPD6650	Approved
0.6992	Remote Similarity	NPD6649	Approved
0.6967	Remote Similarity	NPD6372	Approved
0.6967	Remote Similarity	NPD6373	Approved
0.6949	Remote Similarity	NPD5344	Discontinued
0.6942	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD5697	Approved
0.6923	Remote Similarity	NPD7830	Approved
0.6923	Remote Similarity	NPD7829	Approved
0.6911	Remote Similarity	NPD4634	Approved
0.6911	Remote Similarity	NPD6883	Approved
0.6911	Remote Similarity	NPD7290	Approved
0.6911	Remote Similarity	NPD7102	Approved
0.6899	Remote Similarity	NPD6921	Approved
0.6885	Remote Similarity	NPD7320	Approved
0.687	Remote Similarity	NPD7900	Approved
0.687	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD8130	Phase 1
0.6855	Remote Similarity	NPD6617	Approved
0.6855	Remote Similarity	NPD6869	Approved
0.6855	Remote Similarity	NPD6847	Approved
0.6853	Remote Similarity	NPD7625	Phase 1
0.6842	Remote Similarity	NPD6033	Approved
0.6829	Remote Similarity	NPD6013	Approved
0.6829	Remote Similarity	NPD6014	Approved
0.6829	Remote Similarity	NPD6012	Approved
0.6803	Remote Similarity	NPD5701	Approved
0.6794	Remote Similarity	NPD7604	Phase 2
0.6783	Remote Similarity	NPD6399	Phase 3
0.6777	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD5983	Phase 2
0.6754	Remote Similarity	NPD7838	Discovery
0.6748	Remote Similarity	NPD6011	Approved
0.6696	Remote Similarity	NPD3618	Phase 1
0.6696	Remote Similarity	NPD8035	Phase 2
0.6696	Remote Similarity	NPD6411	Approved
0.6696	Remote Similarity	NPD8034	Phase 2
0.6696	Remote Similarity	NPD7983	Approved
0.6696	Remote Similarity	NPD6079	Approved
0.6695	Remote Similarity	NPD6083	Phase 2
0.6695	Remote Similarity	NPD6084	Phase 2
0.6692	Remote Similarity	NPD6336	Discontinued
0.6667	Remote Similarity	NPD5328	Approved
0.6667	Remote Similarity	NPD6053	Discontinued
0.6667	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6638	Remote Similarity	NPD5779	Approved
0.6638	Remote Similarity	NPD5778	Approved
0.6637	Remote Similarity	NPD3573	Approved
0.6612	Remote Similarity	NPD5211	Phase 2
0.6607	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD1694	Approved
0.6593	Remote Similarity	NPD8336	Approved
0.6593	Remote Similarity	NPD8337	Approved
0.6587	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD6008	Approved
0.6583	Remote Similarity	NPD5286	Approved
0.6583	Remote Similarity	NPD6648	Approved
0.6583	Remote Similarity	NPD5285	Approved
0.6583	Remote Similarity	NPD4696	Approved
0.6579	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD7260	Phase 2
0.6567	Remote Similarity	NPD8451	Approved
0.6555	Remote Similarity	NPD4755	Approved
0.6552	Remote Similarity	NPD7637	Suspended
0.6549	Remote Similarity	NPD7334	Approved
0.6549	Remote Similarity	NPD6409	Approved
0.6549	Remote Similarity	NPD7521	Approved
0.6549	Remote Similarity	NPD6684	Approved
0.6549	Remote Similarity	NPD5330	Approved
0.6549	Remote Similarity	NPD7146	Approved
0.6541	Remote Similarity	NPD7642	Approved
0.6525	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD6101	Approved
0.6519	Remote Similarity	NPD8448	Approved
0.6512	Remote Similarity	NPD6274	Approved
0.6504	Remote Similarity	NPD5141	Approved
0.6496	Remote Similarity	NPD8391	Approved
0.6496	Remote Similarity	NPD4202	Approved
0.6496	Remote Similarity	NPD6914	Discontinued
0.6496	Remote Similarity	NPD8392	Approved
0.6496	Remote Similarity	NPD5956	Approved
0.6496	Remote Similarity	NPD8390	Approved
0.6489	Remote Similarity	NPD7101	Approved
0.6489	Remote Similarity	NPD7100	Approved
0.6475	Remote Similarity	NPD5225	Approved
0.6475	Remote Similarity	NPD5226	Approved
0.6475	Remote Similarity	NPD4633	Approved
0.6475	Remote Similarity	NPD5224	Approved
0.6471	Remote Similarity	NPD5222	Approved
0.6471	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD5221	Approved
0.6466	Remote Similarity	NPD5785	Approved
0.6466	Remote Similarity	NPD8080	Discontinued
0.6462	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6446	Remote Similarity	NPD4700	Approved
0.6435	Remote Similarity	NPD6672	Approved
0.6435	Remote Similarity	NPD5737	Approved
0.6435	Remote Similarity	NPD6903	Approved
0.6423	Remote Similarity	NPD5175	Approved
0.6423	Remote Similarity	NPD5174	Approved
0.6417	Remote Similarity	NPD5173	Approved
0.6412	Remote Similarity	NPD6335	Approved
0.6404	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6403	Remote Similarity	NPD8338	Approved
0.6398	Remote Similarity	NPD7799	Discontinued
0.6393	Remote Similarity	NPD5223	Approved
0.6391	Remote Similarity	NPD8444	Approved
0.6387	Remote Similarity	NPD5695	Phase 3
0.6385	Remote Similarity	NPD6868	Approved
0.6383	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.6372	Remote Similarity	NPD3666	Approved
0.6372	Remote Similarity	NPD4786	Approved
0.6372	Remote Similarity	NPD3133	Approved
0.6372	Remote Similarity	NPD3665	Phase 1
0.637	Remote Similarity	NPD8340	Approved
0.637	Remote Similarity	NPD8342	Approved
0.637	Remote Similarity	NPD8341	Approved
0.637	Remote Similarity	NPD8299	Approved
0.6364	Remote Similarity	NPD5696	Approved
0.6356	Remote Similarity	NPD8171	Discontinued
0.6349	Remote Similarity	NPD4729	Approved
0.6349	Remote Similarity	NPD4730	Approved
0.6339	Remote Similarity	NPD3667	Approved
0.6336	Remote Similarity	NPD6317	Approved
0.6333	Remote Similarity	NPD4697	Phase 3
0.6333	Remote Similarity	NPD7839	Suspended
0.632	Remote Similarity	NPD4767	Approved
0.632	Remote Similarity	NPD4768	Approved
0.6312	Remote Similarity	NPD8415	Approved
0.6303	Remote Similarity	NPD5282	Discontinued
0.6288	Remote Similarity	NPD7641	Discontinued

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