NPASS Compound

Structure

NPC301226 OpenBabel07101718242D 31 35 0 0 1 0 0 0 0 0999 V2000 -5.0518 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3679 -0.9722 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4981 -1.4583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0120 -0.6164 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5259 2.4306 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.9444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8420 1.4583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 0.9722 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6839 -0.9722 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8420 -1.4583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2098 1.4583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6839 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6839 -2.9167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3679 1.9444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8420 -2.4306 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8420 0.4861 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6839 1.9444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8420 1.4583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2098 0.4861 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3679 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6839 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6839 -0.9722 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.9722 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5259 -2.4306 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5259 0.4861 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5259 -1.4583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5259 1.4583 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8420 -1.4583 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8420 0.4861 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3679 -2.9167 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 2 0 0 0 0 3 26 1 0 0 0 0 4 26 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 23 1 0 0 0 0 11 14 1 0 0 0 0 11 19 1 0 0 0 0 12 16 1 0 0 0 0 12 22 1 0 0 0 0 13 15 1 0 0 0 0 13 24 1 0 0 0 0 14 27 1 0 0 0 0 15 28 1 0 0 0 0 16 30 1 0 0 0 0 17 18 1 0 0 0 0 17 27 1 0 0 0 0 18 29 1 0 0 0 0 19 20 1 0 0 0 0 20 2 1 6 0 0 0 20 25 1 0 0 0 0 21 25 1 0 0 0 0 21 29 1 6 0 0 0 22 26 1 0 0 0 0 22 28 1 1 0 0 0 23 28 1 1 0 0 0 23 30 1 0 0 0 0 24 26 1 0 0 0 0 24 31 1 1 0 0 0 25 27 1 6 0 0 0 27 5 1 1 0 0 0 28 6 1 1 0 0 0 29 30 1 1 0 0 0 30 8 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	426.39
Volume:	490.807
LogP:	6.974
LogD:	5.687
LogS:	-6.304
# Rotatable Bonds:	0
TPSA:	20.23
# H-Bond Aceptor:	1
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.389
Synthetic Accessibility Score:	4.842
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:	-5.057
MDCK Permeability:	1.2763629456458148e-05
Pgp-inhibitor:	0.06
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.957
30% Bioavailability (F30%):	0.846

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.085
Plasma Protein Binding (PPB):	95.88555145263672%
Volume Distribution (VD):	1.25
Pgp-substrate:	2.0114500522613525%

ADMET: Metabolism

CYP1A2-inhibitor:	0.057
CYP1A2-substrate:	0.525
CYP2C19-inhibitor:	0.087
CYP2C19-substrate:	0.942
CYP2C9-inhibitor:	0.152
CYP2C9-substrate:	0.446
CYP2D6-inhibitor:	0.135
CYP2D6-substrate:	0.867
CYP3A4-inhibitor:	0.369
CYP3A4-substrate:	0.455

ADMET: Excretion

Clearance (CL):	4.837
Half-life (T1/2):	0.082

ADMET: Toxicity

hERG Blockers:	0.085
Human Hepatotoxicity (H-HT):	0.128
Drug-inuced Liver Injury (DILI):	0.023
AMES Toxicity:	0.002
Rat Oral Acute Toxicity:	0.455
Maximum Recommended Daily Dose:	0.925
Skin Sensitization:	0.652
Carcinogencity:	0.007
Eye Corrosion:	0.943
Eye Irritation:	0.815
Respiratory Toxicity:	0.965

Download Data

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

Natural Product: NPC301226

Natural Product ID:	NPC301226
*Common Name:**	Taraxa-20(30)-En-3-Beta-Ol
IUPAC Name:	(3S,4aR,6aR,6aR,6bR,8aR,12S,12aS,14aR,14bR)-4,4,6a,6b,8a,12,14b-heptamethyl-11-methylidene-1,2,3,4a,5,6,6a,7,8,9,10,12,12a,13,14,14a-hexadecahydropicen-3-ol
Synonyms:
Standard InCHIKey:	XWMMEBCFHUKHEX-CWFQSGEHSA-N
Standard InCHI:	InChI=1S/C30H50O/c1-19-11-14-27(5)17-18-29(7)21(25(27)20(19)2)9-10-23-28(6)15-13-24(31)26(3,4)22(28)12-16-30(23,29)8/h20-25,31H,1,9-18H2,2-8H3/t20-,21-,22+,23-,24+,25+,27-,28+,29-,30-/m1/s1
SMILES:	C=C1CC[C@]2([C@@H]([C@@H]1C)[C@H]1CC[C@H]3[C@@]([C@@]1(CC2)C)(C)CC[C@@H]1[C@]3(C)CC[C@@H](C1(C)C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL497525
PubChem CID:	441686
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
NPO20111	Anthemis auriculata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16643047]
NPO20111	Anthemis auriculata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO20111	Anthemis auriculata	Species	Asteraceae	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
MIC	11

Activity Type	# Activity
Organism	11

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	117400.0	nM	PMID[573430]
NPT172	Organism	Proteus mirabilis	Proteus mirabilis	MIC	=	117400.0	nM	PMID[573430]
NPT141	Organism	Agrobacterium tumefaciens	Agrobacterium tumefaciens	MIC	=	29300.0	nM	PMID[573430]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	=	117400.0	nM	PMID[573430]
NPT3729	Organism	Pseudomonas tolaasii	Pseudomonas tolaasii	MIC	=	117400.0	nM	PMID[573430]
NPT3608	Organism	Salmonella enteritidis	Salmonella enterica subsp. enterica serovar Enteritidis	MIC	=	117400.0	nM	PMID[573430]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	29300.0	nM	PMID[573430]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	=	58700.0	nM	PMID[573430]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	=	14700.0	nM	PMID[573430]
NPT314	Organism	Bacillus cereus	Bacillus cereus	MIC	=	58700.0	nM	PMID[573430]
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	117400.0	nM	PMID[573430]

☑ 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 NPC301226 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	256
0.1-0.2	2878
0.2-0.3	12960
0.3-0.4	13721
0.4-0.5	5052
0.5-0.6	4324
0.6-0.7	2683
0.7-0.8	722
0.8-0.85	49
0.85-0.9	49
0.9-0.95	0
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9851	High Similarity	NPC211009
0.9565	High Similarity	NPC144075
0.9155	High Similarity	NPC122418
0.9155	High Similarity	NPC30590
0.9155	High Similarity	NPC290598
0.9155	High Similarity	NPC265328
0.9155	High Similarity	NPC27765
0.9155	High Similarity	NPC120098
0.9143	High Similarity	NPC62657
0.9143	High Similarity	NPC192638
0.9143	High Similarity	NPC25511
0.9028	High Similarity	NPC157996
0.9028	High Similarity	NPC101475
0.9028	High Similarity	NPC34177
0.9028	High Similarity	NPC40394
0.9014	High Similarity	NPC231256
0.9014	High Similarity	NPC212879
0.9014	High Similarity	NPC240235
0.9014	High Similarity	NPC104387
0.9014	High Similarity	NPC178383
0.9014	High Similarity	NPC34700
0.9014	High Similarity	NPC138374
0.8986	High Similarity	NPC45296
0.8904	High Similarity	NPC470396
0.8904	High Similarity	NPC253807
0.8904	High Similarity	NPC99168
0.8904	High Similarity	NPC474989
0.8904	High Similarity	NPC300499
0.8904	High Similarity	NPC230295
0.8904	High Similarity	NPC98386
0.8904	High Similarity	NPC158662
0.8904	High Similarity	NPC22955
0.8904	High Similarity	NPC196753
0.8889	High Similarity	NPC278091
0.8889	High Similarity	NPC78067
0.8889	High Similarity	NPC14112
0.8889	High Similarity	NPC86305
0.8889	High Similarity	NPC106364
0.8889	High Similarity	NPC93662
0.8873	High Similarity	NPC100334
0.8857	High Similarity	NPC111234
0.8788	High Similarity	NPC290791
0.8788	High Similarity	NPC292419
0.8784	High Similarity	NPC291379
0.8784	High Similarity	NPC53744
0.8767	High Similarity	NPC248830
0.8767	High Similarity	NPC212241
0.8767	High Similarity	NPC202540
0.8767	High Similarity	NPC119355
0.8667	High Similarity	NPC295131
0.8649	High Similarity	NPC102708
0.8649	High Similarity	NPC42853
0.8611	High Similarity	NPC308440
0.8611	High Similarity	NPC49168
0.8611	High Similarity	NPC472503
0.8611	High Similarity	NPC254509
0.8611	High Similarity	NPC5046
0.8611	High Similarity	NPC196358
0.8611	High Similarity	NPC145552
0.8571	High Similarity	NPC210323
0.8553	High Similarity	NPC242350
0.8533	High Similarity	NPC49599
0.8533	High Similarity	NPC80297
0.8533	High Similarity	NPC49627
0.8533	High Similarity	NPC116119
0.8533	High Similarity	NPC475727
0.8533	High Similarity	NPC472742
0.8514	High Similarity	NPC472805
0.8514	High Similarity	NPC90979
0.8493	Intermediate Similarity	NPC200243
0.8493	Intermediate Similarity	NPC185536
0.8493	Intermediate Similarity	NPC70982
0.8493	Intermediate Similarity	NPC230704
0.8493	Intermediate Similarity	NPC3403
0.8472	Intermediate Similarity	NPC195489
0.8472	Intermediate Similarity	NPC182717
0.8442	Intermediate Similarity	NPC47763
0.8442	Intermediate Similarity	NPC304285
0.8429	Intermediate Similarity	NPC2648
0.8421	Intermediate Similarity	NPC475679
0.8406	Intermediate Similarity	NPC473929
0.84	Intermediate Similarity	NPC72507
0.8382	Intermediate Similarity	NPC68656
0.8382	Intermediate Similarity	NPC101128
0.8382	Intermediate Similarity	NPC144650
0.8378	Intermediate Similarity	NPC470766
0.8378	Intermediate Similarity	NPC237460
0.8378	Intermediate Similarity	NPC91573
0.8333	Intermediate Similarity	NPC159168
0.8333	Intermediate Similarity	NPC253402
0.8333	Intermediate Similarity	NPC167706
0.8312	Intermediate Similarity	NPC116202
0.8286	Intermediate Similarity	NPC269077
0.8286	Intermediate Similarity	NPC185874
0.8286	Intermediate Similarity	NPC253303
0.8286	Intermediate Similarity	NPC139207
0.8286	Intermediate Similarity	NPC204233
0.8267	Intermediate Similarity	NPC257191
0.8267	Intermediate Similarity	NPC470758
0.8267	Intermediate Similarity	NPC307336
0.8267	Intermediate Similarity	NPC260301
0.8267	Intermediate Similarity	NPC138502
0.8267	Intermediate Similarity	NPC331618
0.8267	Intermediate Similarity	NPC84868
0.8267	Intermediate Similarity	NPC470711
0.8261	Intermediate Similarity	NPC282619
0.8261	Intermediate Similarity	NPC27243
0.8261	Intermediate Similarity	NPC11555
0.8261	Intermediate Similarity	NPC60837
0.8261	Intermediate Similarity	NPC2728
0.8261	Intermediate Similarity	NPC476737
0.8261	Intermediate Similarity	NPC172613
0.8261	Intermediate Similarity	NPC208198
0.825	Intermediate Similarity	NPC187545
0.8228	Intermediate Similarity	NPC238992
0.8169	Intermediate Similarity	NPC475893
0.8169	Intermediate Similarity	NPC94192
0.8169	Intermediate Similarity	NPC469987
0.8169	Intermediate Similarity	NPC244790
0.8158	Intermediate Similarity	NPC244385
0.8158	Intermediate Similarity	NPC477817
0.8158	Intermediate Similarity	NPC472501
0.8158	Intermediate Similarity	NPC6978
0.8158	Intermediate Similarity	NPC302041
0.8158	Intermediate Similarity	NPC138621
0.8158	Intermediate Similarity	NPC31828
0.8158	Intermediate Similarity	NPC167037
0.8158	Intermediate Similarity	NPC285761
0.8158	Intermediate Similarity	NPC85346
0.8158	Intermediate Similarity	NPC312328
0.8158	Intermediate Similarity	NPC301707
0.8158	Intermediate Similarity	NPC472500
0.8158	Intermediate Similarity	NPC65897
0.8158	Intermediate Similarity	NPC472499
0.8158	Intermediate Similarity	NPC477819
0.8158	Intermediate Similarity	NPC472342
0.8143	Intermediate Similarity	NPC475897
0.8133	Intermediate Similarity	NPC470749
0.8133	Intermediate Similarity	NPC189883
0.8133	Intermediate Similarity	NPC38141
0.8125	Intermediate Similarity	NPC133954
0.8125	Intermediate Similarity	NPC191965
0.8108	Intermediate Similarity	NPC476736
0.8108	Intermediate Similarity	NPC91858
0.8108	Intermediate Similarity	NPC477138
0.8108	Intermediate Similarity	NPC243342
0.8101	Intermediate Similarity	NPC5280
0.8101	Intermediate Similarity	NPC237795
0.8101	Intermediate Similarity	NPC82538
0.8101	Intermediate Similarity	NPC475726
0.8101	Intermediate Similarity	NPC472743
0.8101	Intermediate Similarity	NPC246956
0.8082	Intermediate Similarity	NPC110799
0.8082	Intermediate Similarity	NPC164045
0.8077	Intermediate Similarity	NPC328264
0.8056	Intermediate Similarity	NPC9942
0.8052	Intermediate Similarity	NPC80530
0.8052	Intermediate Similarity	NPC273410
0.8052	Intermediate Similarity	NPC24504
0.8052	Intermediate Similarity	NPC476316
0.8052	Intermediate Similarity	NPC472463
0.8026	Intermediate Similarity	NPC471798
0.8025	Intermediate Similarity	NPC137306
0.8025	Intermediate Similarity	NPC475862
0.8025	Intermediate Similarity	NPC95594
0.8025	Intermediate Similarity	NPC213412
0.8025	Intermediate Similarity	NPC237344
0.8025	Intermediate Similarity	NPC74363
0.8025	Intermediate Similarity	NPC477579
0.8025	Intermediate Similarity	NPC84121
0.8025	Intermediate Similarity	NPC235341
0.8	Intermediate Similarity	NPC257347
0.8	Intermediate Similarity	NPC322353
0.8	Intermediate Similarity	NPC291503
0.8	Intermediate Similarity	NPC260116
0.8	Intermediate Similarity	NPC103822
0.8	Intermediate Similarity	NPC477923
0.8	Intermediate Similarity	NPC141071
0.8	Intermediate Similarity	NPC258595
0.8	Intermediate Similarity	NPC80463
0.8	Intermediate Similarity	NPC475745
0.8	Intermediate Similarity	NPC74595
0.8	Intermediate Similarity	NPC474482
0.8	Intermediate Similarity	NPC264665
0.8	Intermediate Similarity	NPC66566
0.8	Intermediate Similarity	NPC471723
0.8	Intermediate Similarity	NPC118508
0.8	Intermediate Similarity	NPC64123
0.8	Intermediate Similarity	NPC121744
0.7975	Intermediate Similarity	NPC248886
0.7973	Intermediate Similarity	NPC471799
0.7973	Intermediate Similarity	NPC472506
0.7949	Intermediate Similarity	NPC322313
0.7949	Intermediate Similarity	NPC236237
0.7949	Intermediate Similarity	NPC13554
0.7949	Intermediate Similarity	NPC71535
0.7949	Intermediate Similarity	NPC47149
0.7949	Intermediate Similarity	NPC78545
0.7949	Intermediate Similarity	NPC102253
0.7945	Intermediate Similarity	NPC145498

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 NPC301226 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	264
0.1-0.2	3123
0.2-0.3	3938
0.3-0.4	1290
0.4-0.5	250
0.5-0.6	212
0.6-0.7	66
0.7-0.8	6
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8784	High Similarity	NPD7645	Phase 2
0.7949	Intermediate Similarity	NPD7525	Registered
0.7901	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7763	Intermediate Similarity	NPD7339	Approved
0.7763	Intermediate Similarity	NPD6942	Approved
0.7558	Intermediate Similarity	NPD7515	Phase 2
0.7436	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD7748	Approved
0.7159	Intermediate Similarity	NPD8034	Phase 2
0.7159	Intermediate Similarity	NPD8035	Phase 2
0.7105	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD3618	Phase 1
0.6962	Remote Similarity	NPD6926	Approved
0.6962	Remote Similarity	NPD6924	Approved
0.6957	Remote Similarity	NPD7902	Approved
0.6941	Remote Similarity	NPD4786	Approved
0.6932	Remote Similarity	NPD5328	Approved
0.6923	Remote Similarity	NPD7151	Approved
0.6923	Remote Similarity	NPD7150	Approved
0.6923	Remote Similarity	NPD7152	Approved
0.6923	Remote Similarity	NPD4243	Approved
0.6905	Remote Similarity	NPD3667	Approved
0.6883	Remote Similarity	NPD6922	Approved
0.6883	Remote Similarity	NPD6923	Approved
0.6824	Remote Similarity	NPD4788	Approved
0.6795	Remote Similarity	NPD4787	Phase 1
0.6795	Remote Similarity	NPD7143	Approved
0.6795	Remote Similarity	NPD7144	Approved
0.679	Remote Similarity	NPD6933	Approved
0.6778	Remote Similarity	NPD6079	Approved
0.675	Remote Similarity	NPD4784	Approved
0.675	Remote Similarity	NPD4785	Approved
0.6709	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7509	Discontinued
0.6667	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8264	Approved
0.6667	Remote Similarity	NPD4748	Discontinued
0.663	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.663	Remote Similarity	NPD7900	Approved
0.6585	Remote Similarity	NPD6117	Approved
0.6552	Remote Similarity	NPD3666	Approved
0.6552	Remote Similarity	NPD3665	Phase 1
0.6552	Remote Similarity	NPD3133	Approved
0.6548	Remote Similarity	NPD6929	Approved
0.6543	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD7638	Approved
0.6522	Remote Similarity	NPD4202	Approved
0.6517	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6515	Remote Similarity	NPD384	Approved
0.6515	Remote Similarity	NPD385	Approved
0.6506	Remote Similarity	NPD6116	Phase 1
0.6471	Remote Similarity	NPD6930	Phase 2
0.6471	Remote Similarity	NPD6931	Approved
0.6463	Remote Similarity	NPD4190	Phase 3
0.6463	Remote Similarity	NPD3703	Phase 2
0.6463	Remote Similarity	NPD5275	Approved
0.6458	Remote Similarity	NPD7639	Approved
0.6458	Remote Similarity	NPD7640	Approved
0.6429	Remote Similarity	NPD6115	Approved
0.6429	Remote Similarity	NPD6697	Approved
0.6429	Remote Similarity	NPD6114	Approved
0.6429	Remote Similarity	NPD6118	Approved
0.6375	Remote Similarity	NPD4244	Approved
0.6375	Remote Similarity	NPD4245	Approved
0.6316	Remote Similarity	NPD5222	Approved
0.6316	Remote Similarity	NPD4697	Phase 3
0.6316	Remote Similarity	NPD5221	Approved
0.6316	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.631	Remote Similarity	NPD6925	Approved
0.631	Remote Similarity	NPD6932	Approved
0.631	Remote Similarity	NPD5776	Phase 2
0.6279	Remote Similarity	NPD6928	Phase 2
0.625	Remote Similarity	NPD5173	Approved
0.625	Remote Similarity	NPD6695	Phase 3
0.625	Remote Similarity	NPD3698	Phase 2
0.625	Remote Similarity	NPD4755	Approved
0.6235	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6235	Remote Similarity	NPD7145	Approved
0.6186	Remote Similarity	NPD5290	Discontinued
0.618	Remote Similarity	NPD3668	Phase 3
0.618	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6173	Remote Similarity	NPD4789	Approved
0.617	Remote Similarity	NPD6399	Phase 3
0.6163	Remote Similarity	NPD6683	Phase 2
0.6163	Remote Similarity	NPD4195	Approved
0.6125	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6125	Remote Similarity	NPD5360	Phase 3
0.6122	Remote Similarity	NPD4696	Approved
0.6122	Remote Similarity	NPD5286	Approved
0.6122	Remote Similarity	NPD5285	Approved
0.6122	Remote Similarity	NPD4700	Approved
0.6111	Remote Similarity	NPD6893	Approved
0.6092	Remote Similarity	NPD7332	Phase 2
0.6092	Remote Similarity	NPD7514	Phase 3
0.6087	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD5223	Approved
0.6047	Remote Similarity	NPD3671	Phase 1
0.6044	Remote Similarity	NPD5279	Phase 3
0.6023	Remote Similarity	NPD6902	Approved
0.6023	Remote Similarity	NPD6898	Phase 1
0.6022	Remote Similarity	NPD4753	Phase 2
0.6022	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5226	Approved
0.6	Remote Similarity	NPD5211	Phase 2
0.6	Remote Similarity	NPD4633	Approved
0.6	Remote Similarity	NPD5225	Approved
0.6	Remote Similarity	NPD7632	Discontinued
0.6	Remote Similarity	NPD5224	Approved
0.598	Remote Similarity	NPD7128	Approved
0.598	Remote Similarity	NPD6402	Approved
0.598	Remote Similarity	NPD5739	Approved
0.598	Remote Similarity	NPD6675	Approved
0.5978	Remote Similarity	NPD7750	Discontinued
0.5978	Remote Similarity	NPD7524	Approved
0.5974	Remote Similarity	NPD368	Approved
0.5955	Remote Similarity	NPD4221	Approved
0.5955	Remote Similarity	NPD4223	Phase 3
0.5949	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.5941	Remote Similarity	NPD4754	Approved
0.5941	Remote Similarity	NPD5175	Approved
0.5941	Remote Similarity	NPD5174	Approved
0.5934	Remote Similarity	NPD5329	Approved
0.5909	Remote Similarity	NPD4695	Discontinued
0.5888	Remote Similarity	NPD8133	Approved
0.5882	Remote Similarity	NPD5141	Approved
0.587	Remote Similarity	NPD7334	Approved
0.587	Remote Similarity	NPD5330	Approved
0.587	Remote Similarity	NPD6684	Approved
0.587	Remote Similarity	NPD7146	Approved
0.587	Remote Similarity	NPD6409	Approved
0.587	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.587	Remote Similarity	NPD7521	Approved
0.5865	Remote Similarity	NPD6899	Approved
0.5865	Remote Similarity	NPD7320	Approved
0.5865	Remote Similarity	NPD6881	Approved
0.5862	Remote Similarity	NPD3617	Approved
0.5859	Remote Similarity	NPD4225	Approved
0.5825	Remote Similarity	NPD4768	Approved
0.5825	Remote Similarity	NPD4767	Approved
0.5824	Remote Similarity	NPD4197	Approved
0.5811	Remote Similarity	NPD342	Phase 1
0.581	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.581	Remote Similarity	NPD6372	Approved
0.581	Remote Similarity	NPD6373	Approved
0.5806	Remote Similarity	NPD3573	Approved
0.5769	Remote Similarity	NPD5697	Approved
0.5769	Remote Similarity	NPD5701	Approved
0.5758	Remote Similarity	NPD6084	Phase 2
0.5758	Remote Similarity	NPD6083	Phase 2
0.5755	Remote Similarity	NPD7102	Approved
0.5755	Remote Similarity	NPD6883	Approved
0.5755	Remote Similarity	NPD7290	Approved
0.5745	Remote Similarity	NPD6903	Approved
0.5743	Remote Similarity	NPD4159	Approved
0.5732	Remote Similarity	NPD6705	Phase 1
0.5729	Remote Similarity	NPD6411	Approved
0.5729	Remote Similarity	NPD7087	Discontinued
0.5727	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD5168	Approved
0.5714	Remote Similarity	NPD4758	Discontinued
0.5714	Remote Similarity	NPD4629	Approved
0.5714	Remote Similarity	NPD6011	Approved
0.5714	Remote Similarity	NPD5210	Approved
0.5714	Remote Similarity	NPD4729	Approved
0.5714	Remote Similarity	NPD8377	Approved
0.5714	Remote Similarity	NPD5128	Approved
0.5714	Remote Similarity	NPD8294	Approved
0.5714	Remote Similarity	NPD4730	Approved
0.5702	Remote Similarity	NPD8328	Phase 3
0.5701	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5701	Remote Similarity	NPD6847	Approved
0.5701	Remote Similarity	NPD6650	Approved
0.5701	Remote Similarity	NPD6649	Approved
0.5701	Remote Similarity	NPD8130	Phase 1
0.5701	Remote Similarity	NPD6617	Approved
0.5701	Remote Similarity	NPD6869	Approved
0.5699	Remote Similarity	NPD5205	Approved
0.5699	Remote Similarity	NPD4623	Approved
0.5699	Remote Similarity	NPD4690	Approved
0.5699	Remote Similarity	NPD4519	Discontinued
0.5699	Remote Similarity	NPD4689	Approved
0.5699	Remote Similarity	NPD4688	Approved
0.5699	Remote Similarity	NPD4693	Phase 3
0.5699	Remote Similarity	NPD4138	Approved
0.5684	Remote Similarity	NPD6051	Approved
0.5679	Remote Similarity	NPD4224	Phase 2
0.5676	Remote Similarity	NPD7328	Approved
0.5676	Remote Similarity	NPD7327	Approved
0.567	Remote Similarity	NPD8171	Discontinued
0.5664	Remote Similarity	NPD8378	Approved
0.5664	Remote Similarity	NPD8033	Approved
0.5664	Remote Similarity	NPD8380	Approved
0.5664	Remote Similarity	NPD8296	Approved
0.5664	Remote Similarity	NPD8379	Approved
0.5664	Remote Similarity	NPD8335	Approved
0.566	Remote Similarity	NPD6012	Approved
0.566	Remote Similarity	NPD6014	Approved
0.566	Remote Similarity	NPD6013	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