NPASS Compound

Structure

NPC473570 OpenBabel07101718292D 39 44 0 0 1 0 0 0 0 0999 V2000 -2.4271 -2.7634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2601 -2.2601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4181 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8200 -1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8966 -1.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0880 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7226 -1.1810 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3559 2.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2219 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3559 -0.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2219 2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9135 -0.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5388 1.1180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9540 2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7045 -2.5823 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6180 -2.1756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -1.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 8.5521 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8200 -0.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3559 1.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.2219 0.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4899 0.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.8200 2.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9511 0.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5388 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.8200 1.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.9540 0.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4899 -0.1910 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.0880 1.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.0880 2.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 8.5521 2.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.6861 -0.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.6861 2.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0880 3.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1045 -1.9945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.6861 0.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9540 -0.1910 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 16 2 0 0 0 0 2 17 1 0 0 0 0 3 18 1 0 0 0 0 4 19 1 0 0 0 0 6 29 1 0 0 0 0 7 12 1 0 0 0 0 7 16 1 0 0 0 0 8 11 1 0 0 0 0 9 10 1 0 0 0 0 9 21 1 0 0 0 0 10 28 1 0 0 0 0 11 30 1 0 0 0 0 13 22 1 0 0 0 0 14 23 1 0 0 0 0 14 30 1 0 0 0 0 15 16 1 0 0 0 0 15 36 1 0 0 0 0 17 25 1 0 0 0 0 17 31 1 6 0 0 0 18 32 2 0 0 0 0 18 37 1 0 0 0 0 19 33 2 0 0 0 0 19 38 1 0 0 0 0 20 8 1 6 0 0 0 20 21 1 0 0 0 0 20 22 1 0 0 0 0 21 29 1 1 0 0 0 22 28 1 1 0 0 0 23 26 1 0 0 0 0 23 34 1 1 0 0 0 24 13 1 1 0 0 0 24 25 1 0 0 0 0 24 39 1 0 0 0 0 25 28 1 1 0 0 0 26 27 1 0 0 0 0 26 37 1 1 0 0 0 27 29 1 1 0 0 0 27 38 1 0 0 0 0 28 5 1 1 0 0 0 29 30 1 1 0 0 0 30 35 1 1 0 0 0 31 12 1 1 0 0 0 31 36 1 0 0 0 0 31 39 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	546.32
Volume:	555.806
LogP:	3.112
LogD:	2.922
LogS:	-4.162
# Rotatable Bonds:	4
TPSA:	111.52
# H-Bond Aceptor:	8
# H-Bond Donor:	2
# Rings:	6
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.396
Synthetic Accessibility Score:	5.916
Fsp3:	0.871
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:	-5.205
MDCK Permeability:	4.977704520570114e-05
Pgp-inhibitor:	0.102
Pgp-substrate:	0.526
Human Intestinal Absorption (HIA):	0.02
20% Bioavailability (F20%):	0.038
30% Bioavailability (F30%):	0.412

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.569
Plasma Protein Binding (PPB):	31.69771957397461%
Volume Distribution (VD):	0.832
Pgp-substrate:	55.77051544189453%

ADMET: Metabolism

CYP1A2-inhibitor:	0.016
CYP1A2-substrate:	0.206
CYP2C19-inhibitor:	0.008
CYP2C19-substrate:	0.352
CYP2C9-inhibitor:	0.012
CYP2C9-substrate:	0.01
CYP2D6-inhibitor:	0.016
CYP2D6-substrate:	0.062
CYP3A4-inhibitor:	0.923
CYP3A4-substrate:	0.299

ADMET: Excretion

Clearance (CL):	4.484
Half-life (T1/2):	0.312

ADMET: Toxicity

hERG Blockers:	0.952
Human Hepatotoxicity (H-HT):	0.8
Drug-inuced Liver Injury (DILI):	0.875
AMES Toxicity:	0.6
Rat Oral Acute Toxicity:	0.93
Maximum Recommended Daily Dose:	0.848
Skin Sensitization:	0.796
Carcinogencity:	0.849
Eye Corrosion:	0.025
Eye Irritation:	0.018
Respiratory Toxicity:	0.982

Download Data

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

Natural Product: NPC473570

Natural Product ID:	NPC473570
*Common Name:**	Tupichigenin Ac
IUPAC Name:	n.a.
Synonyms:	Tupichigenin Ac
Standard InCHIKey:	ORRBQAHWWZOTHR-VKFJXMKWSA-N
Standard InCHI:	InChI=1S/C31H46O8/c1-16-7-12-31(36-15-16)17(2)25-24(39-31)13-22-20-8-11-30(35)14-23(34)26(37-18(3)32)27(38-19(4)33)29(30,6)21(20)9-10-28(22,25)5/h17,20-27,34-35H,1,7-15H2,2-6H3/t17-,20+,21-,22-,23+,24-,25-,26+,27+,28-,29-,30-,31+/m0/s1
SMILES:	CC1C2C(CC3C2(CCC4C3CCC5(C4(C(C(C(C5)O)OC(=O)C)OC(=O)C)C)O)C)OC16CCC(=C)CO6
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL445984
PubChem CID:	10973623
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
NPO31092	Tupistra chinensis	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12608845]
NPO31092	Tupistra chinensis	Species	Asparagaceae	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
Others	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT4162	Cell Line	NUGC	Homo sapiens	Inhibition	=	40.0	%	PMID[533393]

☑ 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 NPC473570 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	277
0.1-0.2	2199
0.2-0.3	6484
0.3-0.4	13236
0.4-0.5	8522
0.5-0.6	5494
0.6-0.7	4021
0.7-0.8	2099
0.8-0.85	281
0.85-0.9	79
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9703	High Similarity	NPC473517
0.94	High Similarity	NPC52585
0.94	High Similarity	NPC228049
0.94	High Similarity	NPC68630
0.902	High Similarity	NPC177701
0.9	High Similarity	NPC274793
0.8932	High Similarity	NPC471467
0.8922	High Similarity	NPC49532
0.8909	High Similarity	NPC83287
0.8857	High Similarity	NPC470169
0.8857	High Similarity	NPC470170
0.8835	High Similarity	NPC31085
0.8818	High Similarity	NPC84987
0.8818	High Similarity	NPC27507
0.8818	High Similarity	NPC471351
0.8818	High Similarity	NPC34390
0.8818	High Similarity	NPC474418
0.8818	High Similarity	NPC471354
0.8818	High Similarity	NPC244402
0.8818	High Similarity	NPC142066
0.8818	High Similarity	NPC157376
0.8818	High Similarity	NPC158344
0.8818	High Similarity	NPC471353
0.8818	High Similarity	NPC473852
0.8818	High Similarity	NPC243196
0.8818	High Similarity	NPC196429
0.8818	High Similarity	NPC77319
0.8818	High Similarity	NPC471355
0.8818	High Similarity	NPC152615
0.8818	High Similarity	NPC309034
0.8818	High Similarity	NPC99728
0.8818	High Similarity	NPC50305
0.8818	High Similarity	NPC87250
0.875	High Similarity	NPC474466
0.875	High Similarity	NPC475136
0.8727	High Similarity	NPC99620
0.8727	High Similarity	NPC193382
0.8727	High Similarity	NPC199428
0.8727	High Similarity	NPC5311
0.8727	High Similarity	NPC310341
0.8725	High Similarity	NPC469725
0.8713	High Similarity	NPC169270
0.8713	High Similarity	NPC292718
0.8713	High Similarity	NPC306797
0.8713	High Similarity	NPC111834
0.8679	High Similarity	NPC54619
0.8661	High Similarity	NPC329905
0.8649	High Similarity	NPC93883
0.8636	High Similarity	NPC84949
0.8636	High Similarity	NPC69576
0.8636	High Similarity	NPC31354
0.8636	High Similarity	NPC471633
0.8614	High Similarity	NPC241047
0.8596	High Similarity	NPC264336
0.8584	High Similarity	NPC475556
0.8584	High Similarity	NPC475629
0.8558	High Similarity	NPC144486
0.8558	High Similarity	NPC471112
0.8545	High Similarity	NPC102619
0.8545	High Similarity	NPC144068
0.8519	High Similarity	NPC475030
0.8519	High Similarity	NPC151134
0.8519	High Similarity	NPC128133
0.8509	High Similarity	NPC314535
0.8509	High Similarity	NPC173555
0.8505	High Similarity	NPC470166
0.85	High Similarity	NPC219516
0.85	High Similarity	NPC130840
0.8496	Intermediate Similarity	NPC29639
0.8496	Intermediate Similarity	NPC5883
0.8496	Intermediate Similarity	NPC44899
0.8496	Intermediate Similarity	NPC236973
0.8496	Intermediate Similarity	NPC469756
0.8496	Intermediate Similarity	NPC30483
0.8496	Intermediate Similarity	NPC470897
0.8496	Intermediate Similarity	NPC304260
0.8496	Intermediate Similarity	NPC292467
0.8496	Intermediate Similarity	NPC55532
0.8496	Intermediate Similarity	NPC32177
0.8491	Intermediate Similarity	NPC475521
0.8482	Intermediate Similarity	NPC203862
0.8482	Intermediate Similarity	NPC290693
0.8462	Intermediate Similarity	NPC317019
0.844	Intermediate Similarity	NPC470867
0.8426	Intermediate Similarity	NPC476513
0.8426	Intermediate Similarity	NPC125324
0.8426	Intermediate Similarity	NPC49032
0.8426	Intermediate Similarity	NPC51172
0.8421	Intermediate Similarity	NPC72260
0.8411	Intermediate Similarity	NPC165405
0.8411	Intermediate Similarity	NPC473199
0.8407	Intermediate Similarity	NPC475403
0.8407	Intermediate Similarity	NPC160888
0.8381	Intermediate Similarity	NPC31346
0.8365	Intermediate Similarity	NPC157739
0.8364	Intermediate Similarity	NPC272242
0.8364	Intermediate Similarity	NPC470311
0.8362	Intermediate Similarity	NPC117445
0.8362	Intermediate Similarity	NPC208193
0.8362	Intermediate Similarity	NPC308262
0.835	Intermediate Similarity	NPC472989
0.8349	Intermediate Similarity	NPC51925
0.8349	Intermediate Similarity	NPC43976
0.8349	Intermediate Similarity	NPC154085
0.8349	Intermediate Similarity	NPC296761
0.8349	Intermediate Similarity	NPC125361
0.8348	Intermediate Similarity	NPC475219
0.8348	Intermediate Similarity	NPC475419
0.8348	Intermediate Similarity	NPC40749
0.8348	Intermediate Similarity	NPC231518
0.8348	Intermediate Similarity	NPC120390
0.8348	Intermediate Similarity	NPC475590
0.8348	Intermediate Similarity	NPC474908
0.8333	Intermediate Similarity	NPC195560
0.8333	Intermediate Similarity	NPC229962
0.8333	Intermediate Similarity	NPC473633
0.8333	Intermediate Similarity	NPC476085
0.8333	Intermediate Similarity	NPC3359
0.8286	Intermediate Similarity	NPC471247
0.8286	Intermediate Similarity	NPC91497
0.8276	Intermediate Similarity	NPC74259
0.8276	Intermediate Similarity	NPC43842
0.8276	Intermediate Similarity	NPC115349
0.8276	Intermediate Similarity	NPC193893
0.8276	Intermediate Similarity	NPC474423
0.8273	Intermediate Similarity	NPC106760
0.8273	Intermediate Similarity	NPC103627
0.8273	Intermediate Similarity	NPC191439
0.8273	Intermediate Similarity	NPC170974
0.8269	Intermediate Similarity	NPC278939
0.8269	Intermediate Similarity	NPC76486
0.8269	Intermediate Similarity	NPC473555
0.8269	Intermediate Similarity	NPC471770
0.8261	Intermediate Similarity	NPC233391
0.8261	Intermediate Similarity	NPC207243
0.8261	Intermediate Similarity	NPC198325
0.8261	Intermediate Similarity	NPC50689
0.8257	Intermediate Similarity	NPC472988
0.8257	Intermediate Similarity	NPC38217
0.8252	Intermediate Similarity	NPC30477
0.8246	Intermediate Similarity	NPC218093
0.8241	Intermediate Similarity	NPC51719
0.8241	Intermediate Similarity	NPC474015
0.8235	Intermediate Similarity	NPC211845
0.8235	Intermediate Similarity	NPC256104
0.8235	Intermediate Similarity	NPC122083
0.8235	Intermediate Similarity	NPC182740
0.8235	Intermediate Similarity	NPC296620
0.8224	Intermediate Similarity	NPC213190
0.8224	Intermediate Similarity	NPC475701
0.8218	Intermediate Similarity	NPC123252
0.8218	Intermediate Similarity	NPC219937
0.8218	Intermediate Similarity	NPC194485
0.8218	Intermediate Similarity	NPC53890
0.8208	Intermediate Similarity	NPC470168
0.8208	Intermediate Similarity	NPC475574
0.8208	Intermediate Similarity	NPC176406
0.8205	Intermediate Similarity	NPC295133
0.8205	Intermediate Similarity	NPC106589
0.8205	Intermediate Similarity	NPC27363
0.8205	Intermediate Similarity	NPC257207
0.8205	Intermediate Similarity	NPC202261
0.82	Intermediate Similarity	NPC473436
0.8198	Intermediate Similarity	NPC65167
0.8198	Intermediate Similarity	NPC13190
0.8198	Intermediate Similarity	NPC114188
0.8182	Intermediate Similarity	NPC91583
0.8182	Intermediate Similarity	NPC474573
0.8182	Intermediate Similarity	NPC473328
0.8182	Intermediate Similarity	NPC240125
0.8182	Intermediate Similarity	NPC473318
0.8182	Intermediate Similarity	NPC28844
0.8174	Intermediate Similarity	NPC291820
0.8174	Intermediate Similarity	NPC81222
0.8173	Intermediate Similarity	NPC156377
0.8165	Intermediate Similarity	NPC471205
0.8165	Intermediate Similarity	NPC234160
0.8165	Intermediate Similarity	NPC226642
0.8165	Intermediate Similarity	NPC122816
0.8158	Intermediate Similarity	NPC20979
0.8158	Intermediate Similarity	NPC476690
0.8158	Intermediate Similarity	NPC100048
0.8155	Intermediate Similarity	NPC113500
0.8155	Intermediate Similarity	NPC3538
0.8155	Intermediate Similarity	NPC477224
0.8151	Intermediate Similarity	NPC469757
0.8151	Intermediate Similarity	NPC179412
0.8151	Intermediate Similarity	NPC146456
0.8151	Intermediate Similarity	NPC471356
0.8151	Intermediate Similarity	NPC471357
0.8151	Intermediate Similarity	NPC117702
0.8148	Intermediate Similarity	NPC475365
0.8148	Intermediate Similarity	NPC31430
0.8148	Intermediate Similarity	NPC85593
0.8148	Intermediate Similarity	NPC474464
0.8131	Intermediate Similarity	NPC470053
0.8125	Intermediate Similarity	NPC473567
0.8125	Intermediate Similarity	NPC473125
0.8125	Intermediate Similarity	NPC231797
0.8125	Intermediate Similarity	NPC243572

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 NPC473570 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	270
0.1-0.2	2500
0.2-0.3	4082
0.3-0.4	1503
0.4-0.5	398
0.5-0.6	269
0.6-0.7	104
0.7-0.8	11
0.8-0.85	10
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9	High Similarity	NPD7516	Approved
0.8909	High Similarity	NPD7328	Approved
0.8909	High Similarity	NPD7327	Approved
0.8509	High Similarity	NPD8378	Approved
0.8509	High Similarity	NPD8380	Approved
0.8509	High Similarity	NPD8379	Approved
0.8509	High Similarity	NPD8296	Approved
0.8509	High Similarity	NPD8335	Approved
0.8421	Intermediate Similarity	NPD8294	Approved
0.8421	Intermediate Similarity	NPD8377	Approved
0.8348	Intermediate Similarity	NPD8033	Approved
0.8214	Intermediate Similarity	NPD8133	Approved
0.8067	Intermediate Similarity	NPD7507	Approved
0.8017	Intermediate Similarity	NPD7319	Approved
0.7881	Intermediate Similarity	NPD7503	Approved
0.7547	Intermediate Similarity	NPD8171	Discontinued
0.74	Intermediate Similarity	NPD6928	Phase 2
0.7364	Intermediate Similarity	NPD7638	Approved
0.7304	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD7639	Approved
0.7297	Intermediate Similarity	NPD7640	Approved
0.7222	Intermediate Similarity	NPD7736	Approved
0.7217	Intermediate Similarity	NPD6412	Phase 2
0.7193	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7155	Intermediate Similarity	NPD6686	Approved
0.712	Intermediate Similarity	NPD7492	Approved
0.7094	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7094	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD6059	Approved
0.7073	Intermediate Similarity	NPD6054	Approved
0.7063	Intermediate Similarity	NPD6616	Approved
0.7008	Intermediate Similarity	NPD8293	Discontinued
0.7008	Intermediate Similarity	NPD7078	Approved
0.6972	Remote Similarity	NPD8034	Phase 2
0.6972	Remote Similarity	NPD8035	Phase 2
0.696	Remote Similarity	NPD6370	Approved
0.6957	Remote Similarity	NPD7625	Phase 1
0.6917	Remote Similarity	NPD6882	Approved
0.6891	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.688	Remote Similarity	NPD6016	Approved
0.688	Remote Similarity	NPD6015	Approved
0.687	Remote Similarity	NPD7632	Discontinued
0.6829	Remote Similarity	NPD6009	Approved
0.6825	Remote Similarity	NPD5988	Approved
0.68	Remote Similarity	NPD6319	Approved
0.6783	Remote Similarity	NPD5344	Discontinued
0.6777	Remote Similarity	NPD8297	Approved
0.6759	Remote Similarity	NPD7524	Approved
0.6746	Remote Similarity	NPD6921	Approved
0.6731	Remote Similarity	NPD7525	Registered
0.6723	Remote Similarity	NPD7320	Approved
0.6721	Remote Similarity	NPD4632	Approved
0.6695	Remote Similarity	NPD7128	Approved
0.6695	Remote Similarity	NPD6675	Approved
0.6695	Remote Similarity	NPD6402	Approved
0.6695	Remote Similarity	NPD5739	Approved
0.6694	Remote Similarity	NPD7115	Discovery
0.6694	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6372	Approved
0.6667	Remote Similarity	NPD6373	Approved
0.6641	Remote Similarity	NPD8328	Phase 3
0.6639	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD6051	Approved
0.6609	Remote Similarity	NPD4225	Approved
0.6583	Remote Similarity	NPD6881	Approved
0.6583	Remote Similarity	NPD6899	Approved
0.6565	Remote Similarity	NPD6033	Approved
0.6557	Remote Similarity	NPD6649	Approved
0.6557	Remote Similarity	NPD6650	Approved
0.6555	Remote Similarity	NPD6008	Approved
0.6512	Remote Similarity	NPD6067	Discontinued
0.65	Remote Similarity	NPD5701	Approved
0.65	Remote Similarity	NPD5697	Approved
0.65	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6496	Remote Similarity	NPD4159	Approved
0.6491	Remote Similarity	NPD7991	Discontinued
0.6484	Remote Similarity	NPD8513	Phase 3
0.6484	Remote Similarity	NPD8515	Approved
0.6484	Remote Similarity	NPD8516	Approved
0.6484	Remote Similarity	NPD8517	Approved
0.6481	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6475	Remote Similarity	NPD7290	Approved
0.6475	Remote Similarity	NPD7102	Approved
0.6475	Remote Similarity	NPD6883	Approved
0.6423	Remote Similarity	NPD6617	Approved
0.6423	Remote Similarity	NPD8130	Phase 1
0.6423	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6423	Remote Similarity	NPD6869	Approved
0.6423	Remote Similarity	NPD6847	Approved
0.641	Remote Similarity	NPD6648	Approved
0.64	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6393	Remote Similarity	NPD6012	Approved
0.6393	Remote Similarity	NPD6013	Approved
0.6393	Remote Similarity	NPD6014	Approved
0.6389	Remote Similarity	NPD6695	Phase 3
0.6385	Remote Similarity	NPD7604	Phase 2
0.6381	Remote Similarity	NPD6118	Approved
0.6381	Remote Similarity	NPD6697	Approved
0.6381	Remote Similarity	NPD6114	Approved
0.6381	Remote Similarity	NPD6115	Approved
0.6379	Remote Similarity	NPD6084	Phase 2
0.6379	Remote Similarity	NPD6083	Phase 2
0.6371	Remote Similarity	NPD6053	Discontinued
0.637	Remote Similarity	NPD8449	Approved
0.6357	Remote Similarity	NPD5983	Phase 2
0.6356	Remote Similarity	NPD1700	Approved
0.6324	Remote Similarity	NPD8450	Suspended
0.6316	Remote Similarity	NPD6399	Phase 3
0.6311	Remote Similarity	NPD6011	Approved
0.629	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6288	Remote Similarity	NPD6336	Discontinued
0.6286	Remote Similarity	NPD6116	Phase 1
0.6239	Remote Similarity	NPD4788	Approved
0.6239	Remote Similarity	NPD4755	Approved
0.6228	Remote Similarity	NPD7637	Suspended
0.622	Remote Similarity	NPD6940	Discontinued
0.621	Remote Similarity	NPD4634	Approved
0.6207	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.619	Remote Similarity	NPD6117	Approved
0.6174	Remote Similarity	NPD4202	Approved
0.6168	Remote Similarity	NPD7645	Phase 2
0.6167	Remote Similarity	NPD5211	Phase 2
0.6161	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6161	Remote Similarity	NPD7750	Discontinued
0.6134	Remote Similarity	NPD5285	Approved
0.6134	Remote Similarity	NPD5286	Approved
0.6134	Remote Similarity	NPD4700	Approved
0.6134	Remote Similarity	NPD4696	Approved
0.6121	Remote Similarity	NPD7748	Approved
0.6119	Remote Similarity	NPD8074	Phase 3
0.6111	Remote Similarity	NPD6931	Approved
0.6111	Remote Similarity	NPD6930	Phase 2
0.6106	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6103	Remote Similarity	NPD5956	Approved
0.6102	Remote Similarity	NPD7902	Approved
0.6098	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6094	Remote Similarity	NPD6274	Approved
0.6091	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6091	Remote Similarity	NPD3669	Approved
0.6087	Remote Similarity	NPD7515	Phase 2
0.6077	Remote Similarity	NPD7101	Approved
0.6077	Remote Similarity	NPD7100	Approved
0.6068	Remote Similarity	NPD5695	Phase 3
0.6066	Remote Similarity	NPD5141	Approved
0.605	Remote Similarity	NPD5696	Approved
0.605	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6038	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6033	Remote Similarity	NPD5224	Approved
0.6033	Remote Similarity	NPD5226	Approved
0.6033	Remote Similarity	NPD4633	Approved
0.6033	Remote Similarity	NPD5225	Approved
0.6019	Remote Similarity	NPD6929	Approved
0.6016	Remote Similarity	NPD4767	Approved
0.6016	Remote Similarity	NPD4768	Approved
0.6	Remote Similarity	NPD6698	Approved
0.6	Remote Similarity	NPD6335	Approved
0.6	Remote Similarity	NPD46	Approved
0.6	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6	Remote Similarity	NPD3168	Discontinued
0.5985	Remote Similarity	NPD6909	Approved
0.5985	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.5985	Remote Similarity	NPD6908	Approved
0.5984	Remote Similarity	NPD5175	Approved
0.5984	Remote Similarity	NPD5174	Approved
0.5982	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.5965	Remote Similarity	NPD6903	Approved
0.5952	Remote Similarity	NPD6371	Approved
0.595	Remote Similarity	NPD5223	Approved
0.5948	Remote Similarity	NPD5693	Phase 1
0.5948	Remote Similarity	NPD7087	Discontinued
0.5943	Remote Similarity	NPD6942	Approved
0.5943	Remote Similarity	NPD7339	Approved
0.5943	Remote Similarity	NPD3702	Approved
0.5929	Remote Similarity	NPD7521	Approved
0.5929	Remote Similarity	NPD6409	Approved
0.5929	Remote Similarity	NPD5330	Approved
0.5929	Remote Similarity	NPD6684	Approved
0.5929	Remote Similarity	NPD7334	Approved
0.5929	Remote Similarity	NPD7146	Approved
0.5923	Remote Similarity	NPD6317	Approved
0.592	Remote Similarity	NPD4729	Approved
0.592	Remote Similarity	NPD4730	Approved
0.5913	Remote Similarity	NPD5328	Approved
0.5913	Remote Similarity	NPD4753	Phase 2
0.59	Remote Similarity	NPD371	Approved
0.5893	Remote Similarity	NPD4786	Approved
0.5888	Remote Similarity	NPD6933	Approved
0.5878	Remote Similarity	NPD6314	Approved
0.5878	Remote Similarity	NPD6313	Approved
0.5877	Remote Similarity	NPD4251	Approved
0.5877	Remote Similarity	NPD4250	Approved
0.5865	Remote Similarity	NPD4787	Phase 1
0.5864	Remote Similarity	NPD7799	Discontinued
0.5862	Remote Similarity	NPD7838	Discovery
0.5854	Remote Similarity	NPD4754	Approved
0.5849	Remote Similarity	NPD1810	Approved
0.5849	Remote Similarity	NPD1811	Approved
0.5847	Remote Similarity	NPD6001	Approved
0.5847	Remote Similarity	NPD7901	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