NPASS Compound

Structure

CID204233 OpenBabel06191715592D 32 36 0 0 1 0 0 0 0 0999 V2000 -3.4641 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2321 -2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 -2.8660 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 3.5000 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 -0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 0 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 -1.7321 3.0000 0.0000 C 0 0 0 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 2.5981 -0.5000 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 -1.7321 -0.0000 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 -0.8660 -0.5000 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 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 2 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 -4.3301 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 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 1 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 0.0000 -0.0000 0.0000 C 0 0 2 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 -5.1962 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 1 0 0 0 0 2 25 1 0 0 0 0 3 25 1 0 0 0 0 7 29 1 0 0 0 0 9 10 1 0 0 0 0 9 21 1 0 0 0 0 10 27 1 0 0 0 0 11 12 1 0 0 0 0 11 25 1 0 0 0 0 12 26 1 0 0 0 0 13 15 1 0 0 0 0 13 26 1 0 0 0 0 14 16 1 0 0 0 0 14 28 1 0 0 0 0 15 29 1 0 0 0 0 16 30 1 0 0 0 0 17 20 1 0 0 0 0 17 22 1 0 0 0 0 18 23 1 0 0 0 0 18 25 1 0 0 0 0 19 24 1 0 0 0 0 19 27 1 6 0 0 0 20 24 1 0 0 0 0 20 31 1 1 0 0 0 21 28 1 6 0 0 0 21 29 1 0 0 0 0 22 27 1 6 0 0 0 22 28 1 0 0 0 0 23 26 1 1 0 0 0 23 30 1 0 0 0 0 24 32 1 6 0 0 0 26 4 1 6 0 0 0 27 5 1 6 0 0 0 28 6 1 6 0 0 0 29 30 1 6 0 0 0 30 8 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	444.4
Volume:	502.234
LogP:	7.026
LogD:	5.259
LogS:	-6.84
# Rotatable Bonds:	0
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.414
Synthetic Accessibility Score:	4.962
Fsp3:	1.0
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:	-4.904
MDCK Permeability:	1.0030437806562986e-05
Pgp-inhibitor:	0.919
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.811
30% Bioavailability (F30%):	0.929

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.046
Plasma Protein Binding (PPB):	95.7719955444336%
Volume Distribution (VD):	1.184
Pgp-substrate:	2.679081439971924%

ADMET: Metabolism

CYP1A2-inhibitor:	0.025
CYP1A2-substrate:	0.366
CYP2C19-inhibitor:	0.035
CYP2C19-substrate:	0.955
CYP2C9-inhibitor:	0.1
CYP2C9-substrate:	0.108
CYP2D6-inhibitor:	0.029
CYP2D6-substrate:	0.24
CYP3A4-inhibitor:	0.36
CYP3A4-substrate:	0.359

ADMET: Excretion

Clearance (CL):	8.004
Half-life (T1/2):	0.107

ADMET: Toxicity

hERG Blockers:	0.985
Human Hepatotoxicity (H-HT):	0.191
Drug-inuced Liver Injury (DILI):	0.078
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.245
Maximum Recommended Daily Dose:	0.044
Skin Sensitization:	0.933
Carcinogencity:	0.08
Eye Corrosion:	0.251
Eye Irritation:	0.069
Respiratory Toxicity:	0.916

Download Data

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

Natural Product: NPC204233

Natural Product ID:	NPC204233
*Common Name:**	Pachysandiol A
IUPAC Name:	(2R,3R,4R,4aS,6aS,6aS,6bR,8aR,12aR,14aS,14bS)-4,4a,6a,6b,8a,11,11,14a-octamethyl-1,2,3,4,5,6,6a,7,8,9,10,12,12a,13,14,14b-hexadecahydropicene-2,3-diol
Synonyms:
Standard InCHIKey:	OFLPXEYYLDOAPP-WXQDRBBESA-N
Standard InCHI:	InChI=1S/C30H52O2/c1-19-24(32)20(31)17-22-27(19,5)10-9-21-28(22,6)14-16-30(8)23-18-25(2,3)11-12-26(23,4)13-15-29(21,30)7/h19-24,31-32H,9-18H2,1-8H3/t19-,20+,21-,22+,23+,24+,26+,27+,28+,29+,30-/m0/s1
SMILES:	C[C@H]1[C@H]([C@@H](C[C@@H]2[C@]1(C)CC[C@H]1[C@@]2(C)CC[C@@]2(C)[C@@H]3CC(C)(C)CC[C@]3(C)CC[C@]12C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL516539
PubChem CID:	21596127
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
NPO13852	Pachysandra terminalis	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22804108]
NPO13852	Pachysandra terminalis	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13852	Pachysandra terminalis	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13852	Pachysandra terminalis	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO13852	Pachysandra terminalis	Species	Buxaceae	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
GI50	5
IC50	1
Others	1

Activity Type	# Activity
Cell Line	5
NON-MOLECULAR	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	GI50	=	66400.0	nM	PMID[529906]
NPT384	Cell Line	TK-10	Homo sapiens	GI50	=	95700.0	nM	PMID[529906]
NPT398	Cell Line	UACC-62	Homo sapiens	GI50	=	83300.0	nM	PMID[529906]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	=	79400.0	nM	PMID[529906]
NPT395	Cell Line	SF-268	Homo sapiens	GI50	=	15500.0	nM	PMID[529906]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	79100.0	nM	PMID[529906]
NPT27	Others	Unspecified		Activity	=	113.0	%	PMID[529906]

☑ 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 NPC204233 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	542
0.1-0.2	5214
0.2-0.3	17908
0.3-0.4	8821
0.4-0.5	4497
0.5-0.6	3459
0.6-0.7	1913
0.7-0.8	308
0.8-0.85	22
0.85-0.9	7
0.9-0.95	3
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9841	High Similarity	NPC475893
0.9365	High Similarity	NPC260116
0.9355	High Similarity	NPC292419
0.9355	High Similarity	NPC290791
0.8955	High Similarity	NPC231945
0.8939	High Similarity	NPC469987
0.8769	High Similarity	NPC80463
0.8636	High Similarity	NPC142712
0.8529	High Similarity	NPC470833
0.8507	High Similarity	NPC48079
0.8429	Intermediate Similarity	NPC253805
0.8429	Intermediate Similarity	NPC282905
0.8429	Intermediate Similarity	NPC68426
0.8429	Intermediate Similarity	NPC477229
0.8429	Intermediate Similarity	NPC211009
0.8382	Intermediate Similarity	NPC472741
0.831	Intermediate Similarity	NPC168511
0.831	Intermediate Similarity	NPC159325
0.8286	Intermediate Similarity	NPC301226
0.8261	Intermediate Similarity	NPC254037
0.8261	Intermediate Similarity	NPC107919
0.8261	Intermediate Similarity	NPC241085
0.8261	Intermediate Similarity	NPC299948
0.8261	Intermediate Similarity	NPC470830
0.8261	Intermediate Similarity	NPC129829
0.8254	Intermediate Similarity	NPC135438
0.8194	Intermediate Similarity	NPC267753
0.8194	Intermediate Similarity	NPC144075
0.8182	Intermediate Similarity	NPC114891
0.8169	Intermediate Similarity	NPC81759
0.8143	Intermediate Similarity	NPC192192
0.8125	Intermediate Similarity	NPC47663
0.8108	Intermediate Similarity	NPC102708
0.8088	Intermediate Similarity	NPC44122
0.8082	Intermediate Similarity	NPC108840
0.806	Intermediate Similarity	NPC167995
0.806	Intermediate Similarity	NPC118937
0.806	Intermediate Similarity	NPC281540
0.806	Intermediate Similarity	NPC159654
0.8056	Intermediate Similarity	NPC477508
0.8056	Intermediate Similarity	NPC130011
0.8056	Intermediate Similarity	NPC10476
0.8056	Intermediate Similarity	NPC228994
0.8056	Intermediate Similarity	NPC192501
0.803	Intermediate Similarity	NPC71460
0.803	Intermediate Similarity	NPC218585
0.803	Intermediate Similarity	NPC148174
0.8028	Intermediate Similarity	NPC127094
0.8	Intermediate Similarity	NPC99264
0.7971	Intermediate Similarity	NPC63190
0.7971	Intermediate Similarity	NPC475884
0.7971	Intermediate Similarity	NPC473230
0.7969	Intermediate Similarity	NPC236588
0.7945	Intermediate Similarity	NPC196136
0.7945	Intermediate Similarity	NPC243027
0.7945	Intermediate Similarity	NPC158208
0.7941	Intermediate Similarity	NPC41577
0.7941	Intermediate Similarity	NPC473276
0.7941	Intermediate Similarity	NPC474380
0.7922	Intermediate Similarity	NPC47763
0.7917	Intermediate Similarity	NPC472341
0.7917	Intermediate Similarity	NPC153719
0.7917	Intermediate Similarity	NPC470610
0.7917	Intermediate Similarity	NPC473238
0.7887	Intermediate Similarity	NPC282454
0.7867	Intermediate Similarity	NPC472608
0.7867	Intermediate Similarity	NPC477577
0.7857	Intermediate Similarity	NPC2568
0.7857	Intermediate Similarity	NPC180777
0.7857	Intermediate Similarity	NPC103647
0.7857	Intermediate Similarity	NPC260319
0.7838	Intermediate Similarity	NPC473916
0.7838	Intermediate Similarity	NPC477601
0.7838	Intermediate Similarity	NPC477602
0.7838	Intermediate Similarity	NPC163597
0.7821	Intermediate Similarity	NPC159168
0.7821	Intermediate Similarity	NPC253402
0.7808	Intermediate Similarity	NPC48795
0.7794	Intermediate Similarity	NPC69149
0.7778	Intermediate Similarity	NPC131506
0.7778	Intermediate Similarity	NPC157422
0.7778	Intermediate Similarity	NPC157777
0.7778	Intermediate Similarity	NPC109457
0.7778	Intermediate Similarity	NPC100586
0.7778	Intermediate Similarity	NPC473279
0.7746	Intermediate Similarity	NPC210323
0.7746	Intermediate Similarity	NPC477820
0.7746	Intermediate Similarity	NPC66407
0.7733	Intermediate Similarity	NPC128951
0.7733	Intermediate Similarity	NPC157996
0.7733	Intermediate Similarity	NPC192046
0.7733	Intermediate Similarity	NPC40394
0.7733	Intermediate Similarity	NPC477227
0.7733	Intermediate Similarity	NPC105208
0.7733	Intermediate Similarity	NPC101475
0.7733	Intermediate Similarity	NPC302578
0.7733	Intermediate Similarity	NPC34177
0.7722	Intermediate Similarity	NPC238992
0.7703	Intermediate Similarity	NPC270306
0.7703	Intermediate Similarity	NPC231256
0.7703	Intermediate Similarity	NPC212879
0.7703	Intermediate Similarity	NPC138374
0.7703	Intermediate Similarity	NPC34700
0.7703	Intermediate Similarity	NPC104387
0.7703	Intermediate Similarity	NPC91387
0.7703	Intermediate Similarity	NPC240235
0.7703	Intermediate Similarity	NPC174964
0.7703	Intermediate Similarity	NPC97534
0.7703	Intermediate Similarity	NPC317242
0.7703	Intermediate Similarity	NPC195155
0.7703	Intermediate Similarity	NPC178383
0.7703	Intermediate Similarity	NPC231680
0.7681	Intermediate Similarity	NPC190827
0.7681	Intermediate Similarity	NPC243469
0.7681	Intermediate Similarity	NPC475943
0.7639	Intermediate Similarity	NPC63588
0.7639	Intermediate Similarity	NPC251201
0.7639	Intermediate Similarity	NPC232925
0.7632	Intermediate Similarity	NPC22955
0.7632	Intermediate Similarity	NPC99168
0.7632	Intermediate Similarity	NPC196753
0.7632	Intermediate Similarity	NPC67657
0.7632	Intermediate Similarity	NPC474989
0.7632	Intermediate Similarity	NPC470396
0.7632	Intermediate Similarity	NPC18857
0.7632	Intermediate Similarity	NPC243594
0.7632	Intermediate Similarity	NPC26029
0.7632	Intermediate Similarity	NPC253807
0.7632	Intermediate Similarity	NPC147993
0.7632	Intermediate Similarity	NPC300499
0.7632	Intermediate Similarity	NPC31031
0.7632	Intermediate Similarity	NPC158662
0.7632	Intermediate Similarity	NPC230295
0.7632	Intermediate Similarity	NPC98386
0.7606	Intermediate Similarity	NPC2648
0.7606	Intermediate Similarity	NPC244790
0.76	Intermediate Similarity	NPC475742
0.76	Intermediate Similarity	NPC278091
0.76	Intermediate Similarity	NPC120098
0.76	Intermediate Similarity	NPC470145
0.76	Intermediate Similarity	NPC30590
0.76	Intermediate Similarity	NPC93662
0.76	Intermediate Similarity	NPC78067
0.76	Intermediate Similarity	NPC122418
0.76	Intermediate Similarity	NPC14112
0.76	Intermediate Similarity	NPC470766
0.76	Intermediate Similarity	NPC5767
0.76	Intermediate Similarity	NPC91573
0.76	Intermediate Similarity	NPC265328
0.76	Intermediate Similarity	NPC86305
0.76	Intermediate Similarity	NPC290598
0.76	Intermediate Similarity	NPC27765
0.7595	Intermediate Similarity	NPC269684
0.7576	Intermediate Similarity	NPC476735
0.7568	Intermediate Similarity	NPC74639
0.7568	Intermediate Similarity	NPC62657
0.7568	Intermediate Similarity	NPC25511
0.7568	Intermediate Similarity	NPC192638
0.7564	Intermediate Similarity	NPC476071
0.7564	Intermediate Similarity	NPC48756
0.7564	Intermediate Similarity	NPC50658
0.7564	Intermediate Similarity	NPC280781
0.7536	Intermediate Similarity	NPC94897
0.7534	Intermediate Similarity	NPC195530
0.7534	Intermediate Similarity	NPC252182
0.7534	Intermediate Similarity	NPC470071
0.7534	Intermediate Similarity	NPC478103
0.7534	Intermediate Similarity	NPC8004
0.7534	Intermediate Similarity	NPC187471
0.7534	Intermediate Similarity	NPC290058
0.7534	Intermediate Similarity	NPC1340
0.7534	Intermediate Similarity	NPC127283
0.7534	Intermediate Similarity	NPC247195
0.7532	Intermediate Similarity	NPC53744
0.7532	Intermediate Similarity	NPC291379
0.7531	Intermediate Similarity	NPC237344
0.75	Intermediate Similarity	NPC119355
0.75	Intermediate Similarity	NPC298168
0.75	Intermediate Similarity	NPC143133
0.75	Intermediate Similarity	NPC64081
0.75	Intermediate Similarity	NPC202540
0.75	Intermediate Similarity	NPC23884
0.75	Intermediate Similarity	NPC248830
0.75	Intermediate Similarity	NPC221420
0.75	Intermediate Similarity	NPC133596
0.75	Intermediate Similarity	NPC185915
0.75	Intermediate Similarity	NPC474574
0.75	Intermediate Similarity	NPC11907
0.75	Intermediate Similarity	NPC212241
0.75	Intermediate Similarity	NPC53209
0.7436	Intermediate Similarity	NPC295131
0.7436	Intermediate Similarity	NPC16449
0.7432	Intermediate Similarity	NPC232112
0.7429	Intermediate Similarity	NPC472946
0.7407	Intermediate Similarity	NPC131350
0.7403	Intermediate Similarity	NPC42853
0.7403	Intermediate Similarity	NPC72507
0.7397	Intermediate Similarity	NPC45296
0.7385	Intermediate Similarity	NPC471269
0.7381	Intermediate Similarity	NPC472146

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 NPC204233 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	604
0.1-0.2	4613
0.2-0.3	2857
0.3-0.4	670
0.4-0.5	254
0.5-0.6	118
0.6-0.7	31
0.7-0.8	3
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8261	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD7645	Phase 2
0.7397	Intermediate Similarity	NPD4787	Phase 1
0.7297	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6117	Approved
0.7105	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD6116	Phase 1
0.7013	Intermediate Similarity	NPD3703	Phase 2
0.6962	Remote Similarity	NPD6697	Approved
0.6962	Remote Similarity	NPD6114	Approved
0.6962	Remote Similarity	NPD6118	Approved
0.6962	Remote Similarity	NPD6115	Approved
0.6935	Remote Similarity	NPD384	Approved
0.6935	Remote Similarity	NPD385	Approved
0.6933	Remote Similarity	NPD4244	Approved
0.6933	Remote Similarity	NPD4245	Approved
0.6806	Remote Similarity	NPD371	Approved
0.68	Remote Similarity	NPD3698	Phase 2
0.679	Remote Similarity	NPD7525	Registered
0.679	Remote Similarity	NPD6928	Phase 2
0.6786	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD4789	Approved
0.6667	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5360	Phase 3
0.6543	Remote Similarity	NPD3671	Phase 1
0.6517	Remote Similarity	NPD7515	Phase 2
0.6486	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD8171	Discontinued
0.6375	Remote Similarity	NPD6942	Approved
0.6375	Remote Similarity	NPD7339	Approved
0.6296	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6234	Remote Similarity	NPD6705	Phase 1
0.6203	Remote Similarity	NPD4758	Discontinued
0.6196	Remote Similarity	NPD7748	Approved
0.6184	Remote Similarity	NPD4224	Phase 2
0.6154	Remote Similarity	NPD8034	Phase 2
0.6154	Remote Similarity	NPD8035	Phase 2
0.6098	Remote Similarity	NPD6933	Approved
0.6044	Remote Similarity	NPD6701	Clinical (unspecified phase)
0.6044	Remote Similarity	NPD6700	Approved
0.6	Remote Similarity	NPD386	Approved
0.6	Remote Similarity	NPD7902	Approved
0.6	Remote Similarity	NPD388	Approved
0.6	Remote Similarity	NPD4748	Discontinued
0.6	Remote Similarity	NPD5777	Approved
0.6	Remote Similarity	NPD6081	Approved
0.5978	Remote Similarity	NPD6702	Approved
0.5978	Remote Similarity	NPD6703	Approved
0.5955	Remote Similarity	NPD3618	Phase 1
0.5952	Remote Similarity	NPD5364	Discontinued
0.5934	Remote Similarity	NPD5328	Approved
0.5909	Remote Similarity	NPD4786	Approved
0.5875	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.5862	Remote Similarity	NPD3667	Approved
0.5854	Remote Similarity	NPD6924	Approved
0.5854	Remote Similarity	NPD1811	Approved
0.5854	Remote Similarity	NPD6926	Approved
0.5854	Remote Similarity	NPD1810	Approved
0.5806	Remote Similarity	NPD6079	Approved
0.58	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.5795	Remote Similarity	NPD4788	Approved
0.5783	Remote Similarity	NPD3702	Approved
0.5728	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.5684	Remote Similarity	NPD7900	Approved
0.5684	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.567	Remote Similarity	NPD7920	Phase 3
0.567	Remote Similarity	NPD7919	Phase 3
0.5657	Remote Similarity	NPD4159	Approved
0.5632	Remote Similarity	NPD7509	Discontinued
0.5625	Remote Similarity	NPD7991	Discontinued
0.5612	Remote Similarity	NPD7638	Approved
0.5612	Remote Similarity	NPD8088	Phase 1
0.561	Remote Similarity	NPD7151	Approved
0.561	Remote Similarity	NPD7150	Approved
0.561	Remote Similarity	NPD7152	Approved
0.561	Remote Similarity	NPD4243	Approved
0.5604	Remote Similarity	NPD8308	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