NPASS Compound

Structure

CID136033 OpenBabel06191715492D 23 24 0 0 1 0 0 0 0 0999 V2000 6.1780 3.5266 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6559 2.7647 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3393 1.7744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6817 2.2014 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2236 1.6864 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2236 -1.6864 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3504 -1.2876 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8994 -0.9211 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2982 1.8201 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1739 1.5498 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3504 1.2876 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1699 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8583 0.9668 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5727 -2.4230 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6970 2.7190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1739 -1.5498 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2571 1.8658 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.8314 -0.4800 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.8994 0.9211 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8314 0.4800 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.0158 -3.2050 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.7761 1.0581 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 15 2 0 0 0 0 2 15 1 0 0 0 0 5 10 2 0 0 0 0 5 11 1 0 0 0 0 6 7 1 0 0 0 0 6 16 1 0 0 0 0 7 18 1 0 0 0 0 8 12 1 0 0 0 0 8 16 2 0 0 0 0 9 13 1 0 0 0 0 9 17 1 0 0 0 0 10 19 1 0 0 0 0 11 20 1 0 0 0 0 12 19 1 0 0 0 0 13 19 1 0 0 0 0 14 16 1 0 0 0 0 14 21 2 0 0 0 0 15 17 1 0 0 0 0 17 22 1 0 0 0 0 18 20 1 6 0 0 0 18 23 1 0 0 0 0 19 3 1 6 0 0 0 20 4 1 6 0 0 0 20 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	318.22
Volume:	353.188
LogP:	3.118
LogD:	3.012
LogS:	-2.545
# Rotatable Bonds:	5
TPSA:	49.83
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.471
Synthetic Accessibility Score:	5.294
Fsp3:	0.65
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.611
MDCK Permeability:	1.385700215905672e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.032
20% Bioavailability (F20%):	0.828
30% Bioavailability (F30%):	0.845

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.28
Plasma Protein Binding (PPB):	72.67236328125%
Volume Distribution (VD):	1.555
Pgp-substrate:	19.043394088745117%

ADMET: Metabolism

CYP1A2-inhibitor:	0.014
CYP1A2-substrate:	0.414
CYP2C19-inhibitor:	0.032
CYP2C19-substrate:	0.827
CYP2C9-inhibitor:	0.032
CYP2C9-substrate:	0.093
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.139
CYP3A4-inhibitor:	0.77
CYP3A4-substrate:	0.394

ADMET: Excretion

Clearance (CL):	6.781
Half-life (T1/2):	0.392

ADMET: Toxicity

hERG Blockers:	0.039
Human Hepatotoxicity (H-HT):	0.556
Drug-inuced Liver Injury (DILI):	0.039
AMES Toxicity:	0.014
Rat Oral Acute Toxicity:	0.034
Maximum Recommended Daily Dose:	0.966
Skin Sensitization:	0.453
Carcinogencity:	0.931
Eye Corrosion:	0.016
Eye Irritation:	0.084
Respiratory Toxicity:	0.97

Download Data

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

Natural Product: NPC136033

Natural Product ID:	NPC136033
*Common Name:**	Vibsanin V
IUPAC Name:	(1S,4E,7S,8E,11S)-7-(3-hydroxy-4-methylpent-4-enyl)-7,11-dimethyl-12-oxabicyclo[9.1.0]dodeca-4,8-diene-4-carbaldehyde
Synonyms:	Vibsanin V
Standard InCHIKey:	ACQYLNJYSCYZAF-JRBVDQLDSA-N
Standard InCHI:	InChI=1S/C20H30O3/c1-15(2)17(22)9-13-19(3)10-5-11-20(4)18(23-20)7-6-16(14-21)8-12-19/h5,8,10,14,17-18,22H,1,6-7,9,11-13H2,2-4H3/b10-5+,16-8+/t17?,18-,19+,20-/m0/s1
SMILES:	O=C/C/1=C/C[C@](C)(CCC(C(=C)C)O)/C=C/C[C@]2([C@H](CC1)O2)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL513707
PubChem CID:	11267134
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000129] Alcohols and polyols [CHEMONTID:0001661] Secondary alcohols

*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
NPO6717	Viburnum awabuki	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15043405]
NPO6717	Viburnum awabuki	Species	Adoxaceae	Eukaryota	n.a.	leaf	n.a.	Database[Article]
NPO6717	Viburnum awabuki	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6717	Viburnum awabuki	Species	Adoxaceae	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
ED50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	ED50	<	10.0	ug ml-1	PMID[452868]

☑ 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 NPC136033 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	193
0.1-0.2	1374
0.2-0.3	6778
0.3-0.4	15378
0.4-0.5	10294
0.5-0.6	6580
0.6-0.7	1958
0.7-0.8	135
0.8-0.85	6
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8514	High Similarity	NPC261398
0.8353	Intermediate Similarity	NPC83423
0.8077	Intermediate Similarity	NPC227814
0.8077	Intermediate Similarity	NPC144995
0.8026	Intermediate Similarity	NPC10758
0.8026	Intermediate Similarity	NPC250928
0.7975	Intermediate Similarity	NPC472256
0.7975	Intermediate Similarity	NPC474011
0.7952	Intermediate Similarity	NPC145963
0.7901	Intermediate Similarity	NPC207186
0.7875	Intermediate Similarity	NPC469646
0.7701	Intermediate Similarity	NPC471738
0.7683	Intermediate Similarity	NPC475994
0.7683	Intermediate Similarity	NPC474056
0.7654	Intermediate Similarity	NPC271070
0.7647	Intermediate Similarity	NPC1761
0.7647	Intermediate Similarity	NPC52609
0.7614	Intermediate Similarity	NPC476704
0.759	Intermediate Similarity	NPC181195
0.759	Intermediate Similarity	NPC261125
0.7586	Intermediate Similarity	NPC122502
0.7568	Intermediate Similarity	NPC228574
0.7568	Intermediate Similarity	NPC294304
0.7561	Intermediate Similarity	NPC476007
0.7561	Intermediate Similarity	NPC276769
0.7556	Intermediate Similarity	NPC475441
0.7529	Intermediate Similarity	NPC279186
0.747	Intermediate Similarity	NPC231739
0.7412	Intermediate Similarity	NPC325031
0.7407	Intermediate Similarity	NPC167049
0.7407	Intermediate Similarity	NPC469691
0.7381	Intermediate Similarity	NPC19900
0.7375	Intermediate Similarity	NPC474884
0.7356	Intermediate Similarity	NPC243618
0.7356	Intermediate Similarity	NPC72464
0.7356	Intermediate Similarity	NPC70424
0.7356	Intermediate Similarity	NPC474865
0.7342	Intermediate Similarity	NPC477448
0.7342	Intermediate Similarity	NPC477449
0.7333	Intermediate Similarity	NPC212598
0.7333	Intermediate Similarity	NPC115179
0.7333	Intermediate Similarity	NPC106040
0.7317	Intermediate Similarity	NPC469678
0.7317	Intermediate Similarity	NPC474885
0.7317	Intermediate Similarity	NPC475771
0.7317	Intermediate Similarity	NPC469669
0.7312	Intermediate Similarity	NPC214694
0.7308	Intermediate Similarity	NPC106613
0.7303	Intermediate Similarity	NPC72513
0.7294	Intermediate Similarity	NPC470945
0.7294	Intermediate Similarity	NPC470947
0.7294	Intermediate Similarity	NPC470946
0.7294	Intermediate Similarity	NPC233377
0.7284	Intermediate Similarity	NPC49737
0.7284	Intermediate Similarity	NPC261316
0.7283	Intermediate Similarity	NPC125180
0.7273	Intermediate Similarity	NPC261380
0.7273	Intermediate Similarity	NPC476426
0.7273	Intermediate Similarity	NPC96621
0.7262	Intermediate Similarity	NPC267231
0.7262	Intermediate Similarity	NPC62336
0.7253	Intermediate Similarity	NPC265856
0.7253	Intermediate Similarity	NPC166554
0.725	Intermediate Similarity	NPC286154
0.7241	Intermediate Similarity	NPC161045
0.7229	Intermediate Similarity	NPC215481
0.7229	Intermediate Similarity	NPC226242
0.7222	Intermediate Similarity	NPC281516
0.7209	Intermediate Similarity	NPC286229
0.7204	Intermediate Similarity	NPC474035
0.7204	Intermediate Similarity	NPC81386
0.7191	Intermediate Similarity	NPC183736
0.7191	Intermediate Similarity	NPC150755
0.7191	Intermediate Similarity	NPC472974
0.7191	Intermediate Similarity	NPC198314
0.7188	Intermediate Similarity	NPC112167
0.7176	Intermediate Similarity	NPC469617
0.7176	Intermediate Similarity	NPC471740
0.7174	Intermediate Similarity	NPC219874
0.7174	Intermediate Similarity	NPC172101
0.7159	Intermediate Similarity	NPC7927
0.7159	Intermediate Similarity	NPC14575
0.7159	Intermediate Similarity	NPC186155
0.7159	Intermediate Similarity	NPC230527
0.7159	Intermediate Similarity	NPC475796
0.7159	Intermediate Similarity	NPC470812
0.7159	Intermediate Similarity	NPC160517
0.7159	Intermediate Similarity	NPC476412
0.7159	Intermediate Similarity	NPC196487
0.7159	Intermediate Similarity	NPC40687
0.7159	Intermediate Similarity	NPC78673
0.7159	Intermediate Similarity	NPC472326
0.7159	Intermediate Similarity	NPC9868
0.7159	Intermediate Similarity	NPC31086
0.7158	Intermediate Similarity	NPC169205
0.7143	Intermediate Similarity	NPC86917
0.7143	Intermediate Similarity	NPC471061
0.7143	Intermediate Similarity	NPC295312
0.7143	Intermediate Similarity	NPC472973
0.7143	Intermediate Similarity	NPC473624
0.7143	Intermediate Similarity	NPC116177
0.7143	Intermediate Similarity	NPC107668
0.7143	Intermediate Similarity	NPC211279
0.7143	Intermediate Similarity	NPC7563
0.7143	Intermediate Similarity	NPC320630
0.7128	Intermediate Similarity	NPC270013
0.7128	Intermediate Similarity	NPC14961
0.7126	Intermediate Similarity	NPC474291
0.7126	Intermediate Similarity	NPC85772
0.7126	Intermediate Similarity	NPC158411
0.7126	Intermediate Similarity	NPC38796
0.7125	Intermediate Similarity	NPC469914
0.7111	Intermediate Similarity	NPC312561
0.7108	Intermediate Similarity	NPC216791
0.7105	Intermediate Similarity	NPC260573
0.7097	Intermediate Similarity	NPC125674
0.7097	Intermediate Similarity	NPC228451
0.7097	Intermediate Similarity	NPC212486
0.7097	Intermediate Similarity	NPC475838
0.7097	Intermediate Similarity	NPC476049
0.7093	Intermediate Similarity	NPC471514
0.7083	Intermediate Similarity	NPC141191
0.7079	Intermediate Similarity	NPC474547
0.7079	Intermediate Similarity	NPC137033
0.7079	Intermediate Similarity	NPC11804
0.7073	Intermediate Similarity	NPC186042
0.7073	Intermediate Similarity	NPC107783
0.7073	Intermediate Similarity	NPC275098
0.7073	Intermediate Similarity	NPC201562
0.7073	Intermediate Similarity	NPC323437
0.7073	Intermediate Similarity	NPC29542
0.7073	Intermediate Similarity	NPC92909
0.7065	Intermediate Similarity	NPC477684
0.7065	Intermediate Similarity	NPC476004
0.7065	Intermediate Similarity	NPC477711
0.7065	Intermediate Similarity	NPC469368
0.7065	Intermediate Similarity	NPC474761
0.7059	Intermediate Similarity	NPC192006
0.7059	Intermediate Similarity	NPC108816
0.7059	Intermediate Similarity	NPC478122
0.7059	Intermediate Similarity	NPC93763
0.7059	Intermediate Similarity	NPC472960
0.7053	Intermediate Similarity	NPC185553
0.7053	Intermediate Similarity	NPC476315
0.7051	Intermediate Similarity	NPC474329
0.7051	Intermediate Similarity	NPC474304
0.7045	Intermediate Similarity	NPC53867
0.7045	Intermediate Similarity	NPC477786
0.7045	Intermediate Similarity	NPC11620
0.7045	Intermediate Similarity	NPC470165
0.7045	Intermediate Similarity	NPC170377
0.7045	Intermediate Similarity	NPC272814
0.7045	Intermediate Similarity	NPC477784
0.7045	Intermediate Similarity	NPC477785
0.7045	Intermediate Similarity	NPC250315
0.7041	Intermediate Similarity	NPC118405
0.7037	Intermediate Similarity	NPC475310
0.7037	Intermediate Similarity	NPC318766
0.7033	Intermediate Similarity	NPC202672
0.7033	Intermediate Similarity	NPC227379
0.7033	Intermediate Similarity	NPC474471
0.7033	Intermediate Similarity	NPC474925
0.7033	Intermediate Similarity	NPC477710
0.7033	Intermediate Similarity	NPC153805
0.7024	Intermediate Similarity	NPC61863
0.7024	Intermediate Similarity	NPC242722
0.7024	Intermediate Similarity	NPC12740
0.7024	Intermediate Similarity	NPC472959
0.7024	Intermediate Similarity	NPC470525
0.7024	Intermediate Similarity	NPC110461
0.7024	Intermediate Similarity	NPC263582
0.7021	Intermediate Similarity	NPC474247
0.7021	Intermediate Similarity	NPC57405
0.7021	Intermediate Similarity	NPC303942
0.7021	Intermediate Similarity	NPC472977
0.7021	Intermediate Similarity	NPC472976
0.7011	Intermediate Similarity	NPC470298
0.7011	Intermediate Similarity	NPC119229
0.701	Intermediate Similarity	NPC174314
0.701	Intermediate Similarity	NPC475053
0.701	Intermediate Similarity	NPC288876
0.7	Intermediate Similarity	NPC475461
0.7	Intermediate Similarity	NPC234038
0.7	Intermediate Similarity	NPC305698
0.7	Intermediate Similarity	NPC61527
0.7	Intermediate Similarity	NPC164393
0.7	Intermediate Similarity	NPC194417
0.7	Intermediate Similarity	NPC305475
0.7	Intermediate Similarity	NPC116575
0.7	Intermediate Similarity	NPC315395
0.7	Intermediate Similarity	NPC316426
0.6989	Remote Similarity	NPC300312
0.6989	Remote Similarity	NPC472978
0.6989	Remote Similarity	NPC261607
0.6989	Remote Similarity	NPC472975
0.6989	Remote Similarity	NPC303697
0.6989	Remote Similarity	NPC111114
0.6989	Remote Similarity	NPC471059
0.6989	Remote Similarity	NPC476705
0.6988	Remote Similarity	NPC215050

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 NPC136033 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	184
0.1-0.2	1994
0.2-0.3	4111
0.3-0.4	2091
0.4-0.5	460
0.5-0.6	271
0.6-0.7	38
0.7-0.8	1
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
0.7179	Intermediate Similarity	NPD7331	Phase 2
0.6947	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD5785	Approved
0.686	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD7154	Phase 3
0.6835	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD1696	Phase 3
0.6703	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD5363	Approved
0.6702	Remote Similarity	NPD6698	Approved
0.6702	Remote Similarity	NPD46	Approved
0.6667	Remote Similarity	NPD5362	Discontinued
0.6632	Remote Similarity	NPD7983	Approved
0.6632	Remote Similarity	NPD6079	Approved
0.6632	Remote Similarity	NPD6411	Approved
0.663	Remote Similarity	NPD5786	Approved
0.6625	Remote Similarity	NPD7341	Phase 2
0.6562	Remote Similarity	NPD5778	Approved
0.6562	Remote Similarity	NPD5779	Approved
0.6556	Remote Similarity	NPD6435	Approved
0.6535	Remote Similarity	NPD5211	Phase 2
0.6495	Remote Similarity	NPD5282	Discontinued
0.6444	Remote Similarity	NPD5369	Approved
0.6421	Remote Similarity	NPD5328	Approved
0.6421	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6421	Remote Similarity	NPD6101	Approved
0.6413	Remote Similarity	NPD3666	Approved
0.6413	Remote Similarity	NPD3133	Approved
0.6413	Remote Similarity	NPD3665	Phase 1
0.6408	Remote Similarity	NPD5141	Approved
0.6374	Remote Similarity	NPD5209	Approved
0.6374	Remote Similarity	NPD3667	Approved
0.6374	Remote Similarity	NPD4270	Approved
0.6374	Remote Similarity	NPD4269	Approved
0.6364	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD5222	Approved
0.6364	Remote Similarity	NPD7839	Suspended
0.6364	Remote Similarity	NPD5221	Approved
0.6364	Remote Similarity	NPD4697	Phase 3
0.6354	Remote Similarity	NPD7838	Discovery
0.6337	Remote Similarity	NPD4696	Approved
0.6337	Remote Similarity	NPD5286	Approved
0.6337	Remote Similarity	NPD5285	Approved
0.6333	Remote Similarity	NPD5368	Approved
0.6333	Remote Similarity	NPD4822	Approved
0.6333	Remote Similarity	NPD4820	Approved
0.6333	Remote Similarity	NPD4821	Approved
0.6333	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD4819	Approved
0.6333	Remote Similarity	NPD4252	Approved
0.6333	Remote Similarity	NPD4695	Discontinued
0.6322	Remote Similarity	NPD8039	Approved
0.63	Remote Similarity	NPD5173	Approved
0.6286	Remote Similarity	NPD5697	Approved
0.6277	Remote Similarity	NPD5279	Phase 3
0.6277	Remote Similarity	NPD3618	Phase 1
0.6277	Remote Similarity	NPD4519	Discontinued
0.6277	Remote Similarity	NPD4623	Approved
0.6275	Remote Similarity	NPD5223	Approved
0.6265	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD6371	Approved
0.6237	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6237	Remote Similarity	NPD4786	Approved
0.6226	Remote Similarity	NPD6899	Approved
0.6226	Remote Similarity	NPD6011	Approved
0.6226	Remote Similarity	NPD6881	Approved
0.6216	Remote Similarity	NPD7115	Discovery
0.6214	Remote Similarity	NPD5225	Approved
0.6214	Remote Similarity	NPD5226	Approved
0.6214	Remote Similarity	NPD5224	Approved
0.6214	Remote Similarity	NPD4633	Approved
0.6211	Remote Similarity	NPD3573	Approved
0.6196	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.618	Remote Similarity	NPD4756	Discovery
0.6173	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.617	Remote Similarity	NPD1694	Approved
0.6168	Remote Similarity	NPD6014	Approved
0.6168	Remote Similarity	NPD6012	Approved
0.6168	Remote Similarity	NPD6013	Approved
0.6154	Remote Similarity	NPD5174	Approved
0.6154	Remote Similarity	NPD5175	Approved
0.6145	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.6145	Remote Similarity	NPD3704	Approved
0.6139	Remote Similarity	NPD4755	Approved
0.6136	Remote Similarity	NPD8264	Approved
0.6129	Remote Similarity	NPD5331	Approved
0.6129	Remote Similarity	NPD5332	Approved
0.6125	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6122	Remote Similarity	NPD7637	Suspended
0.6111	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD6883	Approved
0.6111	Remote Similarity	NPD7290	Approved
0.6111	Remote Similarity	NPD4268	Approved
0.6111	Remote Similarity	NPD4271	Approved
0.6111	Remote Similarity	NPD7102	Approved
0.6105	Remote Similarity	NPD5690	Phase 2
0.61	Remote Similarity	NPD4629	Approved
0.61	Remote Similarity	NPD5210	Approved
0.6098	Remote Similarity	NPD3197	Phase 1
0.6092	Remote Similarity	NPD4732	Discontinued
0.6087	Remote Similarity	NPD4790	Discontinued
0.6082	Remote Similarity	NPD1695	Approved
0.6082	Remote Similarity	NPD4753	Phase 2
0.6078	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6078	Remote Similarity	NPD4225	Approved
0.6061	Remote Similarity	NPD4202	Approved
0.6055	Remote Similarity	NPD6649	Approved
0.6055	Remote Similarity	NPD6869	Approved
0.6055	Remote Similarity	NPD6847	Approved
0.6055	Remote Similarity	NPD6650	Approved
0.6055	Remote Similarity	NPD6617	Approved
0.6055	Remote Similarity	NPD8130	Phase 1
0.6049	Remote Similarity	NPD368	Approved
0.6038	Remote Similarity	NPD6402	Approved
0.6038	Remote Similarity	NPD7128	Approved
0.6038	Remote Similarity	NPD5739	Approved
0.6038	Remote Similarity	NPD6675	Approved
0.6022	Remote Similarity	NPD4223	Phase 3
0.6022	Remote Similarity	NPD4221	Approved
0.6019	Remote Similarity	NPD4700	Approved
0.6	Remote Similarity	NPD7748	Approved
0.6	Remote Similarity	NPD6882	Approved
0.6	Remote Similarity	NPD8297	Approved
0.5981	Remote Similarity	NPD5701	Approved
0.598	Remote Similarity	NPD6083	Phase 2
0.598	Remote Similarity	NPD6084	Phase 2
0.5979	Remote Similarity	NPD4518	Approved
0.5978	Remote Similarity	NPD7514	Phase 3
0.5978	Remote Similarity	NPD7332	Phase 2
0.5962	Remote Similarity	NPD5344	Discontinued
0.596	Remote Similarity	NPD7515	Phase 2
0.5957	Remote Similarity	NPD6695	Phase 3
0.5957	Remote Similarity	NPD6110	Phase 1
0.5941	Remote Similarity	NPD5695	Phase 3
0.5938	Remote Similarity	NPD7146	Approved
0.5938	Remote Similarity	NPD7521	Approved
0.5938	Remote Similarity	NPD6422	Discontinued
0.5938	Remote Similarity	NPD7334	Approved
0.5938	Remote Similarity	NPD6684	Approved
0.5938	Remote Similarity	NPD4249	Approved
0.5938	Remote Similarity	NPD5330	Approved
0.5938	Remote Similarity	NPD6409	Approved
0.5934	Remote Similarity	NPD7145	Approved
0.5926	Remote Similarity	NPD7320	Approved
0.5926	Remote Similarity	NPD4730	Approved
0.5926	Remote Similarity	NPD4729	Approved
0.5914	Remote Similarity	NPD6902	Approved
0.59	Remote Similarity	NPD6399	Phase 3
0.5895	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5895	Remote Similarity	NPD4197	Approved
0.5888	Remote Similarity	NPD6008	Approved
0.5876	Remote Similarity	NPD4251	Approved
0.5876	Remote Similarity	NPD4250	Approved
0.5872	Remote Similarity	NPD6372	Approved
0.5872	Remote Similarity	NPD6373	Approved
0.5865	Remote Similarity	NPD7640	Approved
0.5865	Remote Similarity	NPD7639	Approved
0.5862	Remote Similarity	NPD7143	Approved
0.5862	Remote Similarity	NPD7144	Approved
0.5854	Remote Similarity	NPD4194	Approved
0.5854	Remote Similarity	NPD4192	Approved
0.5854	Remote Similarity	NPD4191	Approved
0.5854	Remote Similarity	NPD4193	Approved
0.5849	Remote Similarity	NPD4754	Approved
0.5844	Remote Similarity	NPD3172	Approved
0.5843	Remote Similarity	NPD6924	Approved
0.5843	Remote Similarity	NPD6926	Approved
0.5833	Remote Similarity	NPD5329	Approved
0.5825	Remote Similarity	NPD7902	Approved
0.5824	Remote Similarity	NPD6925	Approved
0.5824	Remote Similarity	NPD5776	Phase 2
0.5824	Remote Similarity	NPD6932	Approved
0.5823	Remote Similarity	NPD4219	Approved
0.5818	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.5818	Remote Similarity	NPD5250	Approved
0.5818	Remote Similarity	NPD5248	Approved
0.5818	Remote Similarity	NPD5169	Approved
0.5818	Remote Similarity	NPD4634	Approved
0.5818	Remote Similarity	NPD5135	Approved
0.5818	Remote Similarity	NPD5249	Phase 3
0.5818	Remote Similarity	NPD5247	Approved
0.5818	Remote Similarity	NPD5251	Approved
0.5816	Remote Similarity	NPD6903	Approved
0.5816	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5806	Remote Similarity	NPD6930	Phase 2
0.5806	Remote Similarity	NPD6931	Approved
0.5804	Remote Similarity	NPD4632	Approved
0.5795	Remote Similarity	NPD7152	Approved
0.5795	Remote Similarity	NPD7150	Approved
0.5795	Remote Similarity	NPD7151	Approved
0.5789	Remote Similarity	NPD4788	Approved
0.5789	Remote Similarity	NPD6317	Approved
0.578	Remote Similarity	NPD5128	Approved
0.578	Remote Similarity	NPD6686	Approved
0.578	Remote Similarity	NPD5168	Approved
0.5773	Remote Similarity	NPD5280	Approved
0.5773	Remote Similarity	NPD4689	Approved
0.5773	Remote Similarity	NPD4138	Approved
0.5773	Remote Similarity	NPD4688	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