NPASS Compound

Structure

NPC116202 OpenBabel07101718292D 32 37 0 0 1 0 0 0 0 0999 V2000 3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8301 1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 4.5000 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 -1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 2.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 0.0000 C 0 0 1 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 0.8660 2.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 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 -4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 3.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 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 -5.1962 -1.0000 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 3 26 1 0 0 0 0 4 26 1 0 0 0 0 9 13 1 0 0 0 0 9 17 1 0 0 0 0 10 14 1 0 0 0 0 10 20 2 0 0 0 0 11 15 1 0 0 0 0 11 19 1 0 0 0 0 12 16 1 0 0 0 0 12 21 1 0 0 0 0 13 27 1 0 0 0 0 14 27 1 0 0 0 0 15 29 1 0 0 0 0 16 28 1 0 0 0 0 17 1 1 1 0 0 0 17 18 1 0 0 0 0 18 2 1 6 0 0 0 18 23 1 0 0 0 0 19 26 1 0 0 0 0 19 28 1 6 0 0 0 20 29 1 0 0 0 0 20 30 1 0 0 0 0 21 26 1 0 0 0 0 21 31 1 6 0 0 0 22 24 1 0 0 0 0 22 25 1 0 0 0 0 22 32 1 1 0 0 0 23 27 1 1 0 0 0 23 30 1 0 0 0 0 24 28 1 6 0 0 0 24 29 1 0 0 0 0 25 30 1 1 0 0 0 25 32 1 0 0 0 0 27 5 1 6 0 0 0 28 6 1 6 0 0 0 29 7 1 6 0 0 0 30 8 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	440.37
Volume:	491.041
LogP:	7.059
LogD:	5.45
LogS:	-6.134
# Rotatable Bonds:	0
TPSA:	32.76
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	6
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.324
Synthetic Accessibility Score:	5.3
Fsp3:	0.933
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-5.125
MDCK Permeability:	1.5204044757410884e-05
Pgp-inhibitor:	0.983
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.966
30% Bioavailability (F30%):	0.988

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.166
Plasma Protein Binding (PPB):	97.93562316894531%
Volume Distribution (VD):	1.863
Pgp-substrate:	2.1078104972839355%

ADMET: Metabolism

CYP1A2-inhibitor:	0.017
CYP1A2-substrate:	0.357
CYP2C19-inhibitor:	0.07
CYP2C19-substrate:	0.943
CYP2C9-inhibitor:	0.168
CYP2C9-substrate:	0.112
CYP2D6-inhibitor:	0.05
CYP2D6-substrate:	0.364
CYP3A4-inhibitor:	0.827
CYP3A4-substrate:	0.611

ADMET: Excretion

Clearance (CL):	8.676
Half-life (T1/2):	0.162

ADMET: Toxicity

hERG Blockers:	0.123
Human Hepatotoxicity (H-HT):	0.362
Drug-inuced Liver Injury (DILI):	0.039
AMES Toxicity:	0.002
Rat Oral Acute Toxicity:	0.472
Maximum Recommended Daily Dose:	0.928
Skin Sensitization:	0.168
Carcinogencity:	0.014
Eye Corrosion:	0.525
Eye Irritation:	0.129
Respiratory Toxicity:	0.972

Download Data

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

Natural Product: NPC116202

Natural Product ID:	NPC116202
*Common Name:**	GOHBPXGGNXNYEV-PHDYCRKVSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	GOHBPXGGNXNYEV-PHDYCRKVSA-N
Standard InCHI:	InChI=1S/C30H48O2/c1-17-9-13-27(5)14-10-20-29(7)15-11-19-26(3,4)21(31)12-16-28(19,6)24(29)22-25(32-22)30(20,8)23(27)18(17)2/h10,17-19,21-25,31H,9,11-16H2,1-8H3/t17-,18+,19+,21+,22+,23-,24-,25+,27-,28+,29+,30-/m1/s1
SMILES:	C[C@@H]1CC[C@]2([C@@H]([C@H]1C)[C@]1(C)[C@H]3O[C@H]3[C@H]3[C@@](C1=CC2)(C)CC[C@@H]1[C@]3(C)CC[C@@H](C1(C)C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL465912
PubChem CID:	44567515
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001729] Oxepanes

*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
NPO24900	Vladimiria muliensis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[18293903]
NPO24900	Vladimiria muliensis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[19432411]
NPO24900	Vladimiria muliensis	n.a.	n.a.	n.a.	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
MIC	6

Activity Type	# Activity
Organism	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	36300.0	nM	PMID[505552]
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	36300.0	nM	PMID[505552]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	=	36300.0	nM	PMID[505552]
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	MIC	=	36300.0	nM	PMID[505552]
NPT314	Organism	Bacillus cereus	Bacillus cereus	MIC	=	72700.0	nM	PMID[505552]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	72700.0	nM	PMID[505552]

☑ 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 NPC116202 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	233
0.1-0.2	1934
0.2-0.3	7329
0.3-0.4	16721
0.4-0.5	6587
0.5-0.6	5401
0.6-0.7	3475
0.7-0.8	889
0.8-0.85	88
0.85-0.9	27
0.9-0.95	12
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9342	High Similarity	NPC470396
0.9342	High Similarity	NPC99168
0.9342	High Similarity	NPC474989
0.9342	High Similarity	NPC22955
0.9221	High Similarity	NPC53744
0.9221	High Similarity	NPC291379
0.9211	High Similarity	NPC157996
0.9211	High Similarity	NPC101475
0.9211	High Similarity	NPC34177
0.9211	High Similarity	NPC40394
0.92	High Similarity	NPC34700
0.92	High Similarity	NPC138374
0.9091	High Similarity	NPC158662
0.9091	High Similarity	NPC98386
0.9091	High Similarity	NPC300499
0.9091	High Similarity	NPC230295
0.9091	High Similarity	NPC196753
0.9091	High Similarity	NPC253807
0.9079	High Similarity	NPC106364
0.9079	High Similarity	NPC30590
0.9079	High Similarity	NPC265328
0.9079	High Similarity	NPC122418
0.9079	High Similarity	NPC290598
0.9079	High Similarity	NPC27765
0.9079	High Similarity	NPC120098
0.8875	High Similarity	NPC304285
0.8861	High Similarity	NPC295131
0.8846	High Similarity	NPC72507
0.8816	High Similarity	NPC100334
0.878	High Similarity	NPC191965
0.878	High Similarity	NPC477578
0.875	High Similarity	NPC242350
0.8718	High Similarity	NPC472805
0.8718	High Similarity	NPC90979
0.8675	High Similarity	NPC84121
0.8675	High Similarity	NPC137306
0.8659	High Similarity	NPC238992
0.8642	High Similarity	NPC47763
0.8608	High Similarity	NPC476314
0.8571	High Similarity	NPC477138
0.8571	High Similarity	NPC243342
0.8537	High Similarity	NPC159168
0.8537	High Similarity	NPC253402
0.8537	High Similarity	NPC237795
0.8537	High Similarity	NPC82538
0.8481	Intermediate Similarity	NPC471798
0.8462	Intermediate Similarity	NPC291503
0.8462	Intermediate Similarity	NPC477923
0.8462	Intermediate Similarity	NPC66566
0.8452	Intermediate Similarity	NPC237344
0.8442	Intermediate Similarity	NPC471799
0.8442	Intermediate Similarity	NPC182717
0.8442	Intermediate Similarity	NPC211009
0.8415	Intermediate Similarity	NPC248886
0.8372	Intermediate Similarity	NPC470588
0.8354	Intermediate Similarity	NPC106432
0.8353	Intermediate Similarity	NPC73064
0.8333	Intermediate Similarity	NPC471797
0.8333	Intermediate Similarity	NPC91858
0.8333	Intermediate Similarity	NPC133954
0.8313	Intermediate Similarity	NPC132386
0.8312	Intermediate Similarity	NPC167706
0.8312	Intermediate Similarity	NPC301226
0.8312	Intermediate Similarity	NPC242001
0.8312	Intermediate Similarity	NPC110799
0.8293	Intermediate Similarity	NPC195334
0.8293	Intermediate Similarity	NPC142163
0.8293	Intermediate Similarity	NPC108476
0.8293	Intermediate Similarity	NPC290495
0.8276	Intermediate Similarity	NPC471432
0.8276	Intermediate Similarity	NPC471433
0.8276	Intermediate Similarity	NPC474728
0.8272	Intermediate Similarity	NPC472463
0.8256	Intermediate Similarity	NPC470629
0.8256	Intermediate Similarity	NPC290690
0.8256	Intermediate Similarity	NPC181225
0.8256	Intermediate Similarity	NPC473242
0.8256	Intermediate Similarity	NPC246708
0.8256	Intermediate Similarity	NPC474512
0.8256	Intermediate Similarity	NPC40552
0.8256	Intermediate Similarity	NPC17733
0.825	Intermediate Similarity	NPC477924
0.825	Intermediate Similarity	NPC470758
0.825	Intermediate Similarity	NPC91594
0.825	Intermediate Similarity	NPC470711
0.8242	Intermediate Similarity	NPC475876
0.8235	Intermediate Similarity	NPC235341
0.8235	Intermediate Similarity	NPC477579
0.8235	Intermediate Similarity	NPC213412
0.8235	Intermediate Similarity	NPC475862
0.8235	Intermediate Similarity	NPC95594
0.8235	Intermediate Similarity	NPC74363
0.8235	Intermediate Similarity	NPC72638
0.8235	Intermediate Similarity	NPC125399
0.8228	Intermediate Similarity	NPC144075
0.8214	Intermediate Similarity	NPC180834
0.8214	Intermediate Similarity	NPC474047
0.8214	Intermediate Similarity	NPC209802
0.8193	Intermediate Similarity	NPC5985
0.8193	Intermediate Similarity	NPC286786
0.8182	Intermediate Similarity	NPC285184
0.8182	Intermediate Similarity	NPC470590
0.8182	Intermediate Similarity	NPC92801
0.8182	Intermediate Similarity	NPC77099
0.8182	Intermediate Similarity	NPC60755
0.8182	Intermediate Similarity	NPC145498
0.8161	Intermediate Similarity	NPC274330
0.8161	Intermediate Similarity	NPC30522
0.8161	Intermediate Similarity	NPC143232
0.8161	Intermediate Similarity	NPC198664
0.8158	Intermediate Similarity	NPC208999
0.8152	Intermediate Similarity	NPC146188
0.8148	Intermediate Similarity	NPC302041
0.8148	Intermediate Similarity	NPC138621
0.8148	Intermediate Similarity	NPC65897
0.8148	Intermediate Similarity	NPC148977
0.8148	Intermediate Similarity	NPC244385
0.8148	Intermediate Similarity	NPC6978
0.8148	Intermediate Similarity	NPC275910
0.8148	Intermediate Similarity	NPC285761
0.8148	Intermediate Similarity	NPC312328
0.8148	Intermediate Similarity	NPC167037
0.8148	Intermediate Similarity	NPC85346
0.814	Intermediate Similarity	NPC68160
0.814	Intermediate Similarity	NPC102683
0.814	Intermediate Similarity	NPC98442
0.814	Intermediate Similarity	NPC18064
0.814	Intermediate Similarity	NPC307426
0.814	Intermediate Similarity	NPC171203
0.814	Intermediate Similarity	NPC293564
0.814	Intermediate Similarity	NPC242468
0.814	Intermediate Similarity	NPC88716
0.814	Intermediate Similarity	NPC130577
0.814	Intermediate Similarity	NPC142415
0.814	Intermediate Similarity	NPC51700
0.8125	Intermediate Similarity	NPC470749
0.8125	Intermediate Similarity	NPC274079
0.8125	Intermediate Similarity	NPC265588
0.8125	Intermediate Similarity	NPC240604
0.8125	Intermediate Similarity	NPC107059
0.8125	Intermediate Similarity	NPC477925
0.8125	Intermediate Similarity	NPC300324
0.8125	Intermediate Similarity	NPC321016
0.8125	Intermediate Similarity	NPC189883
0.8125	Intermediate Similarity	NPC321381
0.8125	Intermediate Similarity	NPC237460
0.8118	Intermediate Similarity	NPC474189
0.8118	Intermediate Similarity	NPC474349
0.8095	Intermediate Similarity	NPC474789
0.8095	Intermediate Similarity	NPC52108
0.8095	Intermediate Similarity	NPC475789
0.809	Intermediate Similarity	NPC49776
0.809	Intermediate Similarity	NPC63118
0.809	Intermediate Similarity	NPC474436
0.809	Intermediate Similarity	NPC86368
0.8072	Intermediate Similarity	NPC476646
0.8072	Intermediate Similarity	NPC474531
0.8068	Intermediate Similarity	NPC120840
0.8068	Intermediate Similarity	NPC92885
0.8068	Intermediate Similarity	NPC126369
0.8068	Intermediate Similarity	NPC113989
0.8068	Intermediate Similarity	NPC476226
0.8068	Intermediate Similarity	NPC470589
0.8068	Intermediate Similarity	NPC77796
0.8068	Intermediate Similarity	NPC111110
0.8052	Intermediate Similarity	NPC210323
0.8049	Intermediate Similarity	NPC100906
0.8049	Intermediate Similarity	NPC273410
0.8049	Intermediate Similarity	NPC80530
0.8049	Intermediate Similarity	NPC155924
0.8049	Intermediate Similarity	NPC1319
0.8046	Intermediate Similarity	NPC182797
0.8046	Intermediate Similarity	NPC52169
0.8025	Intermediate Similarity	NPC318495
0.8025	Intermediate Similarity	NPC214570
0.8025	Intermediate Similarity	NPC130136
0.8025	Intermediate Similarity	NPC34019
0.8025	Intermediate Similarity	NPC198968
0.8025	Intermediate Similarity	NPC155986
0.8023	Intermediate Similarity	NPC24277
0.8023	Intermediate Similarity	NPC474970
0.8022	Intermediate Similarity	NPC327179
0.8	Intermediate Similarity	NPC28657
0.8	Intermediate Similarity	NPC178383
0.8	Intermediate Similarity	NPC288035
0.8	Intermediate Similarity	NPC215700
0.8	Intermediate Similarity	NPC285893
0.8	Intermediate Similarity	NPC162742
0.8	Intermediate Similarity	NPC141071
0.8	Intermediate Similarity	NPC212879
0.8	Intermediate Similarity	NPC230301
0.8	Intermediate Similarity	NPC104387
0.8	Intermediate Similarity	NPC240235
0.8	Intermediate Similarity	NPC22105
0.8	Intermediate Similarity	NPC257347
0.8	Intermediate Similarity	NPC231256
0.8	Intermediate Similarity	NPC304309
0.8	Intermediate Similarity	NPC136188
0.8	Intermediate Similarity	NPC471723
0.8	Intermediate Similarity	NPC134847

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 NPC116202 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	210
0.1-0.2	2177
0.2-0.3	4171
0.3-0.4	1885
0.4-0.5	365
0.5-0.6	243
0.6-0.7	89
0.7-0.8	9
0.8-0.85	0
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9221	High Similarity	NPD7645	Phase 2
0.8	Intermediate Similarity	NPD6942	Approved
0.8	Intermediate Similarity	NPD7339	Approved
0.7952	Intermediate Similarity	NPD7525	Registered
0.7901	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7802	Intermediate Similarity	NPD7748	Approved
0.7778	Intermediate Similarity	NPD7515	Phase 2
0.7553	Intermediate Similarity	NPD7902	Approved
0.7386	Intermediate Similarity	NPD4786	Approved
0.7356	Intermediate Similarity	NPD3667	Approved
0.7234	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD7900	Approved
0.7229	Intermediate Similarity	NPD6924	Approved
0.7229	Intermediate Similarity	NPD6926	Approved
0.7222	Intermediate Similarity	NPD3618	Phase 1
0.7174	Intermediate Similarity	NPD5328	Approved
0.7143	Intermediate Similarity	NPD8264	Approved
0.7126	Intermediate Similarity	NPD4748	Discontinued
0.7111	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6933	Approved
0.7024	Intermediate Similarity	NPD4784	Approved
0.7024	Intermediate Similarity	NPD4785	Approved
0.7021	Intermediate Similarity	NPD6079	Approved
0.6988	Remote Similarity	NPD7150	Approved
0.6988	Remote Similarity	NPD7151	Approved
0.6988	Remote Similarity	NPD4243	Approved
0.6988	Remote Similarity	NPD7152	Approved
0.6957	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD6923	Approved
0.6951	Remote Similarity	NPD6922	Approved
0.6947	Remote Similarity	NPD6399	Phase 3
0.6939	Remote Similarity	NPD7638	Approved
0.6932	Remote Similarity	NPD7509	Discontinued
0.6889	Remote Similarity	NPD6695	Phase 3
0.6869	Remote Similarity	NPD7639	Approved
0.6869	Remote Similarity	NPD7640	Approved
0.6867	Remote Similarity	NPD7144	Approved
0.6867	Remote Similarity	NPD7143	Approved
0.6842	Remote Similarity	NPD8034	Phase 2
0.6842	Remote Similarity	NPD8035	Phase 2
0.6818	Remote Similarity	NPD6929	Approved
0.6813	Remote Similarity	NPD3666	Approved
0.6813	Remote Similarity	NPD3665	Phase 1
0.6813	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD3133	Approved
0.68	Remote Similarity	NPD4159	Approved
0.6771	Remote Similarity	NPD4202	Approved
0.6742	Remote Similarity	NPD6930	Phase 2
0.6742	Remote Similarity	NPD6931	Approved
0.6702	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.663	Remote Similarity	NPD3668	Phase 3
0.6596	Remote Similarity	NPD7750	Discontinued
0.6596	Remote Similarity	NPD7524	Approved
0.6591	Remote Similarity	NPD6925	Approved
0.6591	Remote Similarity	NPD6932	Approved
0.6591	Remote Similarity	NPD5776	Phase 2
0.6566	Remote Similarity	NPD5222	Approved
0.6566	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD4697	Phase 3
0.6566	Remote Similarity	NPD5221	Approved
0.6552	Remote Similarity	NPD5275	Approved
0.6552	Remote Similarity	NPD4190	Phase 3
0.6548	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD7115	Discovery
0.6538	Remote Similarity	NPD6402	Approved
0.6538	Remote Similarity	NPD5739	Approved
0.6538	Remote Similarity	NPD7128	Approved
0.6538	Remote Similarity	NPD6675	Approved
0.6517	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD7145	Approved
0.65	Remote Similarity	NPD4755	Approved
0.65	Remote Similarity	NPD5173	Approved
0.6495	Remote Similarity	NPD6411	Approved
0.6489	Remote Similarity	NPD7521	Approved
0.6489	Remote Similarity	NPD7334	Approved
0.6489	Remote Similarity	NPD5330	Approved
0.6489	Remote Similarity	NPD6409	Approved
0.6489	Remote Similarity	NPD7146	Approved
0.6489	Remote Similarity	NPD6684	Approved
0.6484	Remote Similarity	NPD6902	Approved
0.6444	Remote Similarity	NPD6683	Phase 2
0.6444	Remote Similarity	NPD4195	Approved
0.6436	Remote Similarity	NPD4225	Approved
0.6436	Remote Similarity	NPD5290	Discontinued
0.6421	Remote Similarity	NPD3573	Approved
0.6415	Remote Similarity	NPD6899	Approved
0.6415	Remote Similarity	NPD7320	Approved
0.6415	Remote Similarity	NPD6881	Approved
0.6408	Remote Similarity	NPD7632	Discontinued
0.6396	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD6893	Approved
0.6374	Remote Similarity	NPD4695	Discontinued
0.6374	Remote Similarity	NPD7332	Phase 2
0.6374	Remote Similarity	NPD7514	Phase 3
0.6373	Remote Similarity	NPD5286	Approved
0.6373	Remote Similarity	NPD5285	Approved
0.6373	Remote Similarity	NPD4700	Approved
0.6373	Remote Similarity	NPD4696	Approved
0.6355	Remote Similarity	NPD6372	Approved
0.6355	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6355	Remote Similarity	NPD6373	Approved
0.6354	Remote Similarity	NPD6903	Approved
0.6337	Remote Similarity	NPD6083	Phase 2
0.6337	Remote Similarity	NPD6084	Phase 2
0.6327	Remote Similarity	NPD7087	Discontinued
0.6321	Remote Similarity	NPD5701	Approved
0.6321	Remote Similarity	NPD5697	Approved
0.6316	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD5279	Phase 3
0.6311	Remote Similarity	NPD5223	Approved
0.6304	Remote Similarity	NPD6898	Phase 1
0.6296	Remote Similarity	NPD7290	Approved
0.6296	Remote Similarity	NPD7102	Approved
0.6296	Remote Similarity	NPD6883	Approved
0.6296	Remote Similarity	NPD368	Approved
0.6289	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD4753	Phase 2
0.6289	Remote Similarity	NPD6101	Approved
0.6289	Remote Similarity	NPD6051	Approved
0.6279	Remote Similarity	NPD4787	Phase 1
0.6262	Remote Similarity	NPD6011	Approved
0.625	Remote Similarity	NPD5225	Approved
0.625	Remote Similarity	NPD4633	Approved
0.625	Remote Similarity	NPD5224	Approved
0.625	Remote Similarity	NPD5211	Phase 2
0.625	Remote Similarity	NPD5226	Approved
0.6239	Remote Similarity	NPD6617	Approved
0.6239	Remote Similarity	NPD8130	Phase 1
0.6239	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD6847	Approved
0.6239	Remote Similarity	NPD6650	Approved
0.6239	Remote Similarity	NPD6649	Approved
0.6239	Remote Similarity	NPD6869	Approved
0.6237	Remote Similarity	NPD4221	Approved
0.6237	Remote Similarity	NPD4223	Phase 3
0.6226	Remote Similarity	NPD6008	Approved
0.6211	Remote Similarity	NPD5329	Approved
0.6207	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD8328	Phase 3
0.6204	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6204	Remote Similarity	NPD6014	Approved
0.6204	Remote Similarity	NPD6013	Approved
0.6204	Remote Similarity	NPD6012	Approved
0.6196	Remote Similarity	NPD6928	Phase 2
0.619	Remote Similarity	NPD5174	Approved
0.619	Remote Similarity	NPD5175	Approved
0.619	Remote Similarity	NPD4754	Approved
0.6186	Remote Similarity	NPD6672	Approved
0.6186	Remote Similarity	NPD5737	Approved
0.6182	Remote Similarity	NPD8297	Approved
0.6182	Remote Similarity	NPD6882	Approved
0.6174	Remote Similarity	NPD8033	Approved
0.617	Remote Similarity	NPD4788	Approved
0.6168	Remote Similarity	NPD6412	Phase 2
0.6163	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6163	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD3617	Approved
0.6139	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6132	Remote Similarity	NPD5141	Approved
0.6111	Remote Similarity	NPD6117	Approved
0.6105	Remote Similarity	NPD4197	Approved
0.6087	Remote Similarity	NPD8294	Approved
0.6087	Remote Similarity	NPD8377	Approved
0.6078	Remote Similarity	NPD7614	Phase 1
0.6075	Remote Similarity	NPD4768	Approved
0.6075	Remote Similarity	NPD4767	Approved
0.6067	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD3168	Discontinued
0.6053	Remote Similarity	NPD7328	Approved
0.6053	Remote Similarity	NPD7327	Approved
0.6044	Remote Similarity	NPD6116	Phase 1
0.6042	Remote Similarity	NPD1696	Phase 3
0.6034	Remote Similarity	NPD8378	Approved
0.6034	Remote Similarity	NPD8296	Approved
0.6034	Remote Similarity	NPD8380	Approved
0.6034	Remote Similarity	NPD8335	Approved
0.6034	Remote Similarity	NPD8379	Approved
0.6022	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6018	Remote Similarity	NPD6868	Approved
0.6	Remote Similarity	NPD7516	Approved
0.6	Remote Similarity	NPD3703	Phase 2
0.6	Remote Similarity	NPD7637	Suspended
0.6	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5344	Discontinued
0.598	Remote Similarity	NPD4629	Approved
0.598	Remote Similarity	NPD5695	Phase 3
0.598	Remote Similarity	NPD5210	Approved
0.5979	Remote Similarity	NPD4623	Approved
0.5979	Remote Similarity	NPD4693	Phase 3
0.5979	Remote Similarity	NPD4519	Discontinued
0.5979	Remote Similarity	NPD6098	Approved
0.5979	Remote Similarity	NPD4690	Approved
0.5979	Remote Similarity	NPD5205	Approved
0.5979	Remote Similarity	NPD4688	Approved
0.5979	Remote Similarity	NPD4689	Approved
0.5979	Remote Similarity	NPD4138	Approved
0.5978	Remote Similarity	NPD6697	Approved
0.5978	Remote Similarity	NPD6118	Approved

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