NPASS Compound

Structure

NPC473616 OpenBabel07101718332D 45 51 0 0 1 0 0 0 0 0999 V2000 11.5444 -5.4269 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0996 -4.0192 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1045 -4.2016 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5000 -4.3301 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0000 -6.9282 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0000 -6.9282 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.1431 -6.4450 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5000 -4.3301 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5000 -4.3301 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.1486 -6.5495 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 -6.0622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 -4.3301 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1691 -6.8053 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.9621 -4.7224 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.5499 -5.5314 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 7.8917 -4.9973 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0000 -1.7321 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5000 -6.0622 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0000 -5.1962 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.5000 -6.0622 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.0000 -5.1962 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.5000 -6.0622 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 7.0827 -6.3986 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5000 -4.3301 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.9781 -5.4041 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5000 -0.8660 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.0000 -1.7321 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5000 -0.8660 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5000 -2.5981 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.0000 -5.1962 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.0000 -5.1962 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 8.5608 -5.7405 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -5.1962 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0000 -1.7321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.9676 -4.8269 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 -2.5981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0000 -3.4641 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.0608 -6.6065 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 2 17 1 0 0 0 0 6 7 1 0 0 0 0 6 19 1 0 0 0 0 8 11 1 0 0 0 0 8 16 1 0 0 0 0 9 10 1 0 0 0 0 9 22 1 0 0 0 0 10 31 1 0 0 0 0 12 19 1 0 0 0 0 12 20 1 0 0 0 0 13 20 1 0 0 0 0 13 25 1 0 0 0 0 14 23 1 0 0 0 0 15 16 1 0 0 0 0 15 40 1 0 0 0 0 16 1 1 1 0 0 0 17 26 1 0 0 0 0 17 33 1 6 0 0 0 18 3 1 1 0 0 0 18 29 1 0 0 0 0 18 41 1 0 0 0 0 19 32 1 1 0 0 0 20 34 1 1 0 0 0 21 7 1 6 0 0 0 21 22 1 0 0 0 0 21 23 1 0 0 0 0 22 32 1 1 0 0 0 23 31 1 1 0 0 0 24 14 1 1 0 0 0 24 26 1 0 0 0 0 24 43 1 0 0 0 0 25 32 1 1 0 0 0 25 42 1 0 0 0 0 26 31 1 1 0 0 0 27 28 1 0 0 0 0 27 29 1 0 0 0 0 27 35 1 1 0 0 0 28 30 1 0 0 0 0 28 36 1 6 0 0 0 29 44 1 1 0 0 0 30 41 1 0 0 0 0 30 42 1 1 0 0 0 31 4 1 1 0 0 0 32 5 1 1 0 0 0 33 11 1 1 0 0 0 33 40 1 0 0 0 0 33 43 1 0 0 0 0 37 45 1 0 0 0 0 38 45 2 0 0 0 0 39 45 2 0 0 0 0 44 45 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	658.34
Volume:	634.63
LogP:	2.849
LogD:	3.12
LogS:	-3.155
# Rotatable Bonds:	4
TPSA:	161.21
# H-Bond Aceptor:	11
# H-Bond Donor:	4
# Rings:	7
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.328
Synthetic Accessibility Score:	6.091
Fsp3:	1.0
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:	-5.462
MDCK Permeability:	3.297079092590138e-05
Pgp-inhibitor:	0.616
Pgp-substrate:	0.334
Human Intestinal Absorption (HIA):	0.824
20% Bioavailability (F20%):	0.031
30% Bioavailability (F30%):	0.729

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.083
Plasma Protein Binding (PPB):	75.29328155517578%
Volume Distribution (VD):	0.825
Pgp-substrate:	7.199675559997559%

ADMET: Metabolism

CYP1A2-inhibitor:	0.004
CYP1A2-substrate:	0.952
CYP2C19-inhibitor:	0.01
CYP2C19-substrate:	0.791
CYP2C9-inhibitor:	0.014
CYP2C9-substrate:	0.018
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.114
CYP3A4-inhibitor:	0.018
CYP3A4-substrate:	0.064

ADMET: Excretion

Clearance (CL):	8.663
Half-life (T1/2):	0.065

ADMET: Toxicity

hERG Blockers:	0.921
Human Hepatotoxicity (H-HT):	0.463
Drug-inuced Liver Injury (DILI):	0.161
AMES Toxicity:	0.028
Rat Oral Acute Toxicity:	0.484
Maximum Recommended Daily Dose:	0.835
Skin Sensitization:	0.951
Carcinogencity:	0.645
Eye Corrosion:	0.777
Eye Irritation:	0.051
Respiratory Toxicity:	0.989

Download Data

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

Natural Product: NPC473616

Natural Product ID:	NPC473616
*Common Name:**	VEBWDEUHONOFKN-GOVPCOKMSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	VEBWDEUHONOFKN-GOVPCOKMSA-N
Standard InCHI:	InChI=1S/C33H54O11S/c1-16-8-11-33(40-15-16)17(2)26-24(43-33)14-23-21-7-6-19-12-20(34)13-25(32(19,5)22(21)9-10-31(23,26)4)42-30-28(36)27(35)29(18(3)41-30)44-45(37,38)39/h16-30,34-36H,6-15H2,1-5H3,(H,37,38,39)/t16-,17-,18-,19-,20+,21+,22-,23-,24-,25+,26-,27-,28-,29+,30+,31-,32-,33+/m0/s1
SMILES:	CC1CCC2(C(C3C(O2)CC4C3(CCC5C4CCC6C5(C(CC(C6)O)OC7C(C(C(C(O7)C)OS(=O)(=O)O)O)O)C)C)C)OC1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL447213
PubChem CID:	10032310
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001013] Steroidal glycosides [CHEMONTID:0002364] Steroidal saponins

*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
NPO32671	chamaedorea linearis	Species	Arecaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8254345]

☑ 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
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	IC12	=	3.5	ug	PMID[485785]

☑ 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 NPC473616 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	617
0.1-0.2	5499
0.2-0.3	14429
0.3-0.4	10393
0.4-0.5	5423
0.5-0.6	3330
0.6-0.7	1891
0.7-0.8	736
0.8-0.85	187
0.85-0.9	69
0.9-0.95	101
0.95-1	22

Similarity Score	Similarity Level	Natural Product ID
0.956	High Similarity	NPC473774
0.956	High Similarity	NPC24960
0.9457	High Similarity	NPC469710
0.9451	High Similarity	NPC149400
0.9451	High Similarity	NPC88962
0.9451	High Similarity	NPC144790
0.9362	High Similarity	NPC473638
0.9348	High Similarity	NPC473503
0.9348	High Similarity	NPC475436
0.9348	High Similarity	NPC473851
0.9348	High Similarity	NPC179859
0.9348	High Similarity	NPC253268
0.9348	High Similarity	NPC252253
0.9348	High Similarity	NPC45959
0.9348	High Similarity	NPC131693
0.9348	High Similarity	NPC174024
0.9348	High Similarity	NPC291547
0.9348	High Similarity	NPC312678
0.9341	High Similarity	NPC204881
0.9341	High Similarity	NPC473830
0.9341	High Similarity	NPC476668
0.9341	High Similarity	NPC473637
0.9255	High Similarity	NPC477223
0.9255	High Similarity	NPC477222
0.9239	High Similarity	NPC477451
0.9239	High Similarity	NPC477547
0.9239	High Similarity	NPC234352
0.9239	High Similarity	NPC250393
0.9239	High Similarity	NPC177834
0.9239	High Similarity	NPC48339
0.9239	High Similarity	NPC297348
0.9239	High Similarity	NPC141769
0.9239	High Similarity	NPC325828
0.9239	High Similarity	NPC476669
0.9239	High Similarity	NPC167644
0.9239	High Similarity	NPC311246
0.9239	High Similarity	NPC249204
0.9231	High Similarity	NPC65550
0.9231	High Similarity	NPC473542
0.9167	High Similarity	NPC477225
0.9149	High Similarity	NPC476510
0.9149	High Similarity	NPC139271
0.9149	High Similarity	NPC473287
0.9149	High Similarity	NPC121453
0.9149	High Similarity	NPC304011
0.9149	High Similarity	NPC142264
0.914	High Similarity	NPC309866
0.914	High Similarity	NPC477224
0.914	High Similarity	NPC294686
0.914	High Similarity	NPC217205
0.914	High Similarity	NPC475325
0.914	High Similarity	NPC471464
0.914	High Similarity	NPC291203
0.914	High Similarity	NPC264101
0.914	High Similarity	NPC3538
0.914	High Similarity	NPC113500
0.914	High Similarity	NPC222731
0.913	High Similarity	NPC149966
0.913	High Similarity	NPC307167
0.913	High Similarity	NPC5632
0.913	High Similarity	NPC229801
0.913	High Similarity	NPC210759
0.9053	High Similarity	NPC475207
0.9053	High Similarity	NPC476112
0.9053	High Similarity	NPC233649
0.9053	High Similarity	NPC307534
0.9053	High Similarity	NPC470028
0.9043	High Similarity	NPC107962
0.9043	High Similarity	NPC19400
0.9043	High Similarity	NPC107188
0.9043	High Similarity	NPC473610
0.9043	High Similarity	NPC474399
0.9043	High Similarity	NPC206003
0.9043	High Similarity	NPC473727
0.9043	High Similarity	NPC6295
0.9043	High Similarity	NPC475351
0.9043	High Similarity	NPC92196
0.9043	High Similarity	NPC211354
0.9032	High Similarity	NPC473726
0.9032	High Similarity	NPC137004
0.9032	High Similarity	NPC172838
0.9022	High Similarity	NPC279329
0.9011	High Similarity	NPC281004
0.8969	High Similarity	NPC475574
0.8958	High Similarity	NPC473518
0.8947	High Similarity	NPC470864
0.8947	High Similarity	NPC195297
0.8947	High Similarity	NPC116756
0.8947	High Similarity	NPC232037
0.8947	High Similarity	NPC284104
0.8947	High Similarity	NPC160426
0.8947	High Similarity	NPC184617
0.8947	High Similarity	NPC287483
0.8947	High Similarity	NPC30856
0.8947	High Similarity	NPC97700
0.8947	High Similarity	NPC98018
0.8947	High Similarity	NPC473601
0.8947	High Similarity	NPC128572
0.8947	High Similarity	NPC470863
0.8947	High Similarity	NPC84111
0.8947	High Similarity	NPC103616
0.8947	High Similarity	NPC296936
0.8947	High Similarity	NPC132080
0.8947	High Similarity	NPC470865
0.8947	High Similarity	NPC475643
0.8947	High Similarity	NPC475625
0.8947	High Similarity	NPC470866
0.8936	High Similarity	NPC175
0.8936	High Similarity	NPC305418
0.8925	High Similarity	NPC36372
0.8925	High Similarity	NPC293609
0.8913	High Similarity	NPC102725
0.8913	High Similarity	NPC20822
0.8913	High Similarity	NPC131466
0.8913	High Similarity	NPC82955
0.8913	High Similarity	NPC473472
0.8854	High Similarity	NPC470862
0.8854	High Similarity	NPC83137
0.8854	High Similarity	NPC232611
0.8854	High Similarity	NPC274200
0.8854	High Similarity	NPC115165
0.8854	High Similarity	NPC51520
0.8854	High Similarity	NPC303069
0.8854	High Similarity	NPC470861
0.8842	High Similarity	NPC473067
0.8842	High Similarity	NPC473064
0.8842	High Similarity	NPC473065
0.883	High Similarity	NPC277774
0.8817	High Similarity	NPC223143
0.8776	High Similarity	NPC472081
0.8776	High Similarity	NPC476512
0.8776	High Similarity	NPC108227
0.8763	High Similarity	NPC291548
0.875	High Similarity	NPC203434
0.875	High Similarity	NPC237071
0.875	High Similarity	NPC238796
0.8696	High Similarity	NPC43912
0.8696	High Similarity	NPC140446
0.8687	High Similarity	NPC134967
0.8687	High Similarity	NPC114700
0.8687	High Similarity	NPC470029
0.8687	High Similarity	NPC310138
0.866	High Similarity	NPC470591
0.8646	High Similarity	NPC477494
0.8627	High Similarity	NPC475634
0.86	High Similarity	NPC476837
0.86	High Similarity	NPC97260
0.86	High Similarity	NPC139181
0.8544	High Similarity	NPC474573
0.8542	High Similarity	NPC30687
0.8526	High Similarity	NPC59006
0.8495	Intermediate Similarity	NPC472396
0.8478	Intermediate Similarity	NPC273290
0.8478	Intermediate Similarity	NPC232044
0.8478	Intermediate Similarity	NPC290612
0.8469	Intermediate Similarity	NPC210157
0.8454	Intermediate Similarity	NPC94582
0.8454	Intermediate Similarity	NPC57964
0.84	Intermediate Similarity	NPC476839
0.84	Intermediate Similarity	NPC476838
0.837	Intermediate Similarity	NPC227260
0.8352	Intermediate Similarity	NPC470611
0.8352	Intermediate Similarity	NPC296734
0.8333	Intermediate Similarity	NPC475521
0.8316	Intermediate Similarity	NPC228059
0.8302	Intermediate Similarity	NPC475312
0.83	Intermediate Similarity	NPC470030
0.83	Intermediate Similarity	NPC20028
0.8298	Intermediate Similarity	NPC161928
0.8298	Intermediate Similarity	NPC210658
0.8257	Intermediate Similarity	NPC476692
0.8257	Intermediate Similarity	NPC476691
0.8252	Intermediate Similarity	NPC215408
0.8247	Intermediate Similarity	NPC323231
0.8247	Intermediate Similarity	NPC171741
0.8247	Intermediate Similarity	NPC224003
0.8247	Intermediate Similarity	NPC470623
0.8247	Intermediate Similarity	NPC18724
0.8218	Intermediate Similarity	NPC477172
0.8218	Intermediate Similarity	NPC478106
0.8211	Intermediate Similarity	NPC128475
0.8191	Intermediate Similarity	NPC471240
0.8182	Intermediate Similarity	NPC156377
0.8173	Intermediate Similarity	NPC54619
0.8173	Intermediate Similarity	NPC473469
0.8163	Intermediate Similarity	NPC77717
0.8163	Intermediate Similarity	NPC471373
0.8163	Intermediate Similarity	NPC151214
0.8163	Intermediate Similarity	NPC148593
0.8163	Intermediate Similarity	NPC191915
0.8163	Intermediate Similarity	NPC267238
0.8163	Intermediate Similarity	NPC253611
0.8155	Intermediate Similarity	NPC475365
0.8137	Intermediate Similarity	NPC80191
0.8137	Intermediate Similarity	NPC310031
0.8132	Intermediate Similarity	NPC257296
0.8132	Intermediate Similarity	NPC7479
0.8132	Intermediate Similarity	NPC248944
0.8119	Intermediate Similarity	NPC41843
0.81	Intermediate Similarity	NPC76486

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 NPC473616 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	552
0.1-0.2	4785
0.2-0.3	2722
0.3-0.4	586
0.4-0.5	330
0.5-0.6	134
0.6-0.7	25
0.7-0.8	13
0.8-0.85	1
0.85-0.9	1
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9239	High Similarity	NPD8171	Discontinued
0.8333	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.8132	Intermediate Similarity	NPD6928	Phase 2
0.7414	Intermediate Similarity	NPD8296	Approved
0.7414	Intermediate Similarity	NPD8380	Approved
0.7414	Intermediate Similarity	NPD8335	Approved
0.7414	Intermediate Similarity	NPD8379	Approved
0.7414	Intermediate Similarity	NPD8378	Approved
0.7328	Intermediate Similarity	NPD8377	Approved
0.7328	Intermediate Similarity	NPD8294	Approved
0.7265	Intermediate Similarity	NPD8033	Approved
0.7212	Intermediate Similarity	NPD7991	Discontinued
0.7155	Intermediate Similarity	NPD7328	Approved
0.7155	Intermediate Similarity	NPD7327	Approved
0.7105	Intermediate Similarity	NPD8133	Approved
0.7094	Intermediate Similarity	NPD7516	Approved
0.6848	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD1811	Approved
0.6737	Remote Similarity	NPD1810	Approved
0.6613	Remote Similarity	NPD7507	Approved
0.6609	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD7319	Approved
0.6579	Remote Similarity	NPD6412	Phase 2
0.6557	Remote Similarity	NPD7503	Approved
0.65	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6434	Remote Similarity	NPD8449	Approved
0.6421	Remote Similarity	NPD2254	Approved
0.6421	Remote Similarity	NPD2686	Approved
0.6421	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6421	Remote Similarity	NPD2687	Approved
0.6417	Remote Similarity	NPD6940	Discontinued
0.6385	Remote Similarity	NPD8450	Suspended
0.6379	Remote Similarity	NPD8174	Phase 2
0.6378	Remote Similarity	NPD7736	Approved
0.6311	Remote Similarity	NPD3669	Approved
0.6311	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.63	Remote Similarity	NPD6697	Approved
0.63	Remote Similarity	NPD6114	Approved
0.63	Remote Similarity	NPD6115	Approved
0.63	Remote Similarity	NPD6118	Approved
0.625	Remote Similarity	NPD4787	Phase 1
0.624	Remote Similarity	NPD6370	Approved
0.62	Remote Similarity	NPD6116	Phase 1
0.619	Remote Similarity	NPD8328	Phase 3
0.6172	Remote Similarity	NPD8293	Discontinued
0.6129	Remote Similarity	NPD371	Approved
0.61	Remote Similarity	NPD6117	Approved
0.608	Remote Similarity	NPD6059	Approved
0.608	Remote Similarity	NPD6054	Approved
0.6063	Remote Similarity	NPD6067	Discontinued
0.6055	Remote Similarity	NPD6701	Clinical (unspecified phase)
0.6055	Remote Similarity	NPD6700	Approved
0.6	Remote Similarity	NPD6702	Approved
0.6	Remote Similarity	NPD6703	Approved
0.5957	Remote Similarity	NPD7625	Phase 1
0.5906	Remote Similarity	NPD6015	Approved
0.5906	Remote Similarity	NPD6016	Approved
0.59	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.5891	Remote Similarity	NPD7492	Approved
0.5865	Remote Similarity	NPD7525	Registered
0.5862	Remote Similarity	NPD1700	Approved
0.5859	Remote Similarity	NPD5988	Approved
0.5859	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.5859	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.5856	Remote Similarity	NPD8034	Phase 2
0.5856	Remote Similarity	NPD8035	Phase 2
0.5846	Remote Similarity	NPD6616	Approved
0.5842	Remote Similarity	NPD3703	Phase 2
0.5833	Remote Similarity	NPD6686	Approved
0.5802	Remote Similarity	NPD7078	Approved
0.5758	Remote Similarity	NPD4244	Approved
0.5758	Remote Similarity	NPD4245	Approved
0.5714	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.569	Remote Similarity	NPD7638	Approved
0.5686	Remote Similarity	NPD3702	Approved
0.566	Remote Similarity	NPD1780	Approved
0.566	Remote Similarity	NPD1779	Approved
0.5657	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.5657	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.5657	Remote Similarity	NPD3698	Phase 2
0.5645	Remote Similarity	NPD6882	Approved
0.5645	Remote Similarity	NPD8297	Approved
0.5641	Remote Similarity	NPD7639	Approved
0.5641	Remote Similarity	NPD7640	Approved
0.5639	Remote Similarity	NPD6033	Approved
0.5638	Remote Similarity	NPD6123	Approved
0.5636	Remote Similarity	NPD7524	Approved
0.5619	Remote Similarity	NPD7645	Phase 2
0.5603	Remote Similarity	NPD7920	Phase 3
0.5603	Remote Similarity	NPD7919	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