NPASS Compound

Structure

NPC470002 OpenBabel07101718282D 33 38 0 0 1 0 0 0 0 0999 V2000 1.0345 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -2.0747 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0413 -1.7215 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9073 -1.2215 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.2052 -2.1351 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4621 -1.4659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7575 -1.4659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8914 -0.9659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.7985 -3.0486 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6450 -1.6569 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2934 -2.4659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2437 -3.8042 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0608 -3.6132 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5961 -1.9659 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 4.7575 -2.4659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1594 -2.9659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0254 -1.4659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9019 -2.3260 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 3.0254 -2.4659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8914 -2.9659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0939 -4.0486 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2934 -1.4659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9073 -2.2215 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1098 -3.3042 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 5.5006 -3.1351 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 4.0993 -3.9441 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 8.8040 -2.9441 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 7.6976 -4.1132 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.1594 -3.9659 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5939 -4.9146 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.6921 -4.0087 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.2908 -5.0267 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1594 -0.9659 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 22 1 0 0 0 0 2 22 1 0 0 0 0 3 23 1 0 0 0 0 4 23 1 0 0 0 0 5 6 1 0 0 0 0 5 9 1 0 0 0 0 6 14 1 0 0 0 0 7 8 2 0 0 0 0 7 15 1 0 0 0 0 8 17 1 0 0 0 0 9 27 1 0 0 0 0 10 14 1 0 0 0 0 10 18 1 0 0 0 0 11 16 1 0 0 0 0 11 22 1 0 0 0 0 12 24 1 0 0 0 0 12 25 1 0 0 0 0 13 24 1 0 0 0 0 13 27 1 0 0 0 0 14 27 1 0 0 0 0 15 20 2 0 0 0 0 15 25 1 0 0 0 0 16 19 1 0 0 0 0 16 29 2 0 0 0 0 17 19 2 0 0 0 0 17 33 1 0 0 0 0 18 23 1 0 0 0 0 18 24 1 0 0 0 0 19 20 1 0 0 0 0 20 26 1 0 0 0 0 21 25 1 0 0 0 0 21 26 2 0 0 0 0 21 30 1 0 0 0 0 22 33 1 0 0 0 0 23 25 1 0 0 0 0 24 28 1 0 0 0 0 28 31 2 0 0 0 0 28 32 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	453.23
Volume:	450.74
LogP:	3.733
LogD:	3.323
LogS:	-5.32
# Rotatable Bonds:	1
TPSA:	101.78
# H-Bond Aceptor:	8
# H-Bond Donor:	1
# Rings:	6
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.515
Synthetic Accessibility Score:	5.202
Fsp3:	0.68
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.2
MDCK Permeability:	5.035848153056577e-05
Pgp-inhibitor:	0.017
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.015
20% Bioavailability (F20%):	0.641
30% Bioavailability (F30%):	0.519

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.129
Plasma Protein Binding (PPB):	74.98168182373047%
Volume Distribution (VD):	1.009
Pgp-substrate:	27.032127380371094%

ADMET: Metabolism

CYP1A2-inhibitor:	0.011
CYP1A2-substrate:	0.546
CYP2C19-inhibitor:	0.102
CYP2C19-substrate:	0.834
CYP2C9-inhibitor:	0.208
CYP2C9-substrate:	0.389
CYP2D6-inhibitor:	0.096
CYP2D6-substrate:	0.247
CYP3A4-inhibitor:	0.87
CYP3A4-substrate:	0.86

ADMET: Excretion

Clearance (CL):	7.159
Half-life (T1/2):	0.16

ADMET: Toxicity

hERG Blockers:	0.395
Human Hepatotoxicity (H-HT):	0.829
Drug-inuced Liver Injury (DILI):	0.186
AMES Toxicity:	0.019
Rat Oral Acute Toxicity:	0.649
Maximum Recommended Daily Dose:	0.952
Skin Sensitization:	0.051
Carcinogencity:	0.903
Eye Corrosion:	0.003
Eye Irritation:	0.006
Respiratory Toxicity:	0.938

Download Data

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

Natural Product: NPC470002

Natural Product ID:	NPC470002
*Common Name:**	Citrinaline B
IUPAC Name:	(5aS,7S,8aR,9aR)-7',7',8,8-tetramethyl-5a-nitrospiro[1,2,3,5,6,8a,9,9a-octahydrocyclopenta[f]indolizine-7,3'-1,8-dihydropyrano[2,3-g]indole]-2',9'-dione;2,2,2-trifluoroacetic acid
Synonyms:	Citrinaline B
Standard InCHIKey:	VYZWJJQVBXKRKP-GKWKSMPMSA-N
Standard InCHI:	InChI=1S/C25H31N3O5.C2HF3O2/c1-22(2)11-16(29)19-17(33-22)8-7-15-20(19)26-21(30)25(15)12-24(28(31)32)13-27-9-5-6-14(27)10-18(24)23(25,3)4;3-2(4,5)1(6)7/h7-8,14,18H,5-6,9-13H2,1-4H3,(H,26,30);(H,6,7)/t14-,18-,24-,25+;/m1./s1
SMILES:	CC1(CC(=O)C2=C(O1)C=CC3=C2NC(=O)C34CC5(CN6CCCC6CC5C4(C)C)[N+](=O)[O-])C.C(=O)(C(F)(F)F)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1642248
PubChem CID:	50900041
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0003522] 2,2-dimethyl-1-benzopyrans

*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
NPO32680	penicillium species.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21053938]

☑ 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
IC50	1
MIC	3

Activity Type	# Activity
NON-MOLECULAR	1
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	32.0	ug.mL-1	PMID[523584]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	32.0	ug.mL-1	PMID[523584]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	32.0	ug.mL-1	PMID[523584]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	194000.0	nM	PMID[523584]

☑ 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 NPC470002 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	384
0.1-0.2	1802
0.2-0.3	6613
0.3-0.4	11548
0.4-0.5	12871
0.5-0.6	8949
0.6-0.7	489
0.7-0.8	34
0.8-0.85	2
0.85-0.9	3
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC470001
0.8116	Intermediate Similarity	NPC205926
0.8075	Intermediate Similarity	NPC37957
0.7952	Intermediate Similarity	NPC476651
0.7907	Intermediate Similarity	NPC153923
0.7668	Intermediate Similarity	NPC470821
0.7613	Intermediate Similarity	NPC266994
0.7557	Intermediate Similarity	NPC71539
0.7557	Intermediate Similarity	NPC250960
0.7545	Intermediate Similarity	NPC74216
0.7524	Intermediate Similarity	NPC204970
0.7512	Intermediate Similarity	NPC174629
0.7403	Intermediate Similarity	NPC49583
0.7343	Intermediate Similarity	NPC473008
0.7302	Intermediate Similarity	NPC14339
0.7273	Intermediate Similarity	NPC473004
0.7235	Intermediate Similarity	NPC198160
0.7227	Intermediate Similarity	NPC116178
0.7225	Intermediate Similarity	NPC28510
0.7195	Intermediate Similarity	NPC217903
0.7195	Intermediate Similarity	NPC321166
0.715	Intermediate Similarity	NPC473007
0.713	Intermediate Similarity	NPC15987
0.7123	Intermediate Similarity	NPC230313
0.7031	Intermediate Similarity	NPC115588
0.7023	Intermediate Similarity	NPC234933
0.7014	Intermediate Similarity	NPC477160
0.6996	Remote Similarity	NPC305542
0.6996	Remote Similarity	NPC244543
0.6995	Remote Similarity	NPC203972
0.6974	Remote Similarity	NPC329830
0.6964	Remote Similarity	NPC30749
0.6963	Remote Similarity	NPC243626
0.696	Remote Similarity	NPC219397
0.6957	Remote Similarity	NPC39822
0.692	Remote Similarity	NPC151171
0.6861	Remote Similarity	NPC471561
0.6854	Remote Similarity	NPC473569
0.685	Remote Similarity	NPC133817
0.685	Remote Similarity	NPC476443
0.6847	Remote Similarity	NPC212123
0.6847	Remote Similarity	NPC478075
0.6818	Remote Similarity	NPC473005
0.6818	Remote Similarity	NPC288759
0.681	Remote Similarity	NPC122886
0.6802	Remote Similarity	NPC477161
0.6798	Remote Similarity	NPC470069
0.6798	Remote Similarity	NPC52059
0.6791	Remote Similarity	NPC114039
0.6791	Remote Similarity	NPC206109
0.6789	Remote Similarity	NPC100863
0.6787	Remote Similarity	NPC41216
0.6781	Remote Similarity	NPC476436
0.6758	Remote Similarity	NPC241263
0.6757	Remote Similarity	NPC301292
0.6757	Remote Similarity	NPC313112
0.6744	Remote Similarity	NPC1820
0.6742	Remote Similarity	NPC474077
0.674	Remote Similarity	NPC473006
0.6727	Remote Similarity	NPC67904
0.6726	Remote Similarity	NPC218303
0.6726	Remote Similarity	NPC82541
0.6711	Remote Similarity	NPC176113
0.6699	Remote Similarity	NPC127082
0.6698	Remote Similarity	NPC474059
0.6696	Remote Similarity	NPC127996
0.6683	Remote Similarity	NPC310403
0.6683	Remote Similarity	NPC148468
0.6683	Remote Similarity	NPC97380
0.6683	Remote Similarity	NPC243673
0.6683	Remote Similarity	NPC63210
0.6683	Remote Similarity	NPC263709
0.6682	Remote Similarity	NPC28368
0.6682	Remote Similarity	NPC327005
0.6667	Remote Similarity	NPC329329
0.6667	Remote Similarity	NPC22476
0.6667	Remote Similarity	NPC204867
0.6667	Remote Similarity	NPC317709
0.664	Remote Similarity	NPC133609
0.6639	Remote Similarity	NPC476429
0.6637	Remote Similarity	NPC168250
0.6622	Remote Similarity	NPC232600
0.6621	Remote Similarity	NPC303214
0.6613	Remote Similarity	NPC189079
0.661	Remote Similarity	NPC13249
0.6608	Remote Similarity	NPC269449
0.6608	Remote Similarity	NPC474366
0.6607	Remote Similarity	NPC87714
0.6595	Remote Similarity	NPC108826
0.6591	Remote Similarity	NPC470021
0.6591	Remote Similarity	NPC272706
0.6579	Remote Similarity	NPC471532
0.6579	Remote Similarity	NPC295479
0.6579	Remote Similarity	NPC220241
0.6574	Remote Similarity	NPC217294
0.6567	Remote Similarity	NPC318525
0.6567	Remote Similarity	NPC10653
0.6564	Remote Similarity	NPC475133
0.6555	Remote Similarity	NPC276993
0.6555	Remote Similarity	NPC298851
0.6555	Remote Similarity	NPC293255
0.6555	Remote Similarity	NPC181138
0.6555	Remote Similarity	NPC210415
0.6555	Remote Similarity	NPC21752
0.6553	Remote Similarity	NPC71205
0.6553	Remote Similarity	NPC299582
0.6552	Remote Similarity	NPC211525
0.6552	Remote Similarity	NPC153694
0.655	Remote Similarity	NPC10732
0.655	Remote Similarity	NPC264176
0.6545	Remote Similarity	NPC170333
0.6544	Remote Similarity	NPC283207
0.6538	Remote Similarity	NPC46259
0.6537	Remote Similarity	NPC234772
0.6535	Remote Similarity	NPC161827
0.6532	Remote Similarity	NPC207239
0.6528	Remote Similarity	NPC21425
0.6526	Remote Similarity	NPC270301
0.6514	Remote Similarity	NPC203628
0.6511	Remote Similarity	NPC106593
0.6509	Remote Similarity	NPC313327
0.6502	Remote Similarity	NPC131486
0.6496	Remote Similarity	NPC140311
0.6495	Remote Similarity	NPC98197
0.6494	Remote Similarity	NPC189661
0.6489	Remote Similarity	NPC473460
0.6488	Remote Similarity	NPC473187
0.6483	Remote Similarity	NPC473667
0.6481	Remote Similarity	NPC77777
0.6479	Remote Similarity	NPC298320
0.6478	Remote Similarity	NPC159815
0.6478	Remote Similarity	NPC119722
0.6476	Remote Similarity	NPC470324
0.6473	Remote Similarity	NPC471489
0.6473	Remote Similarity	NPC469732
0.6468	Remote Similarity	NPC7560
0.6468	Remote Similarity	NPC166979
0.6468	Remote Similarity	NPC128476
0.6466	Remote Similarity	NPC471531
0.6462	Remote Similarity	NPC9475
0.646	Remote Similarity	NPC163829
0.646	Remote Similarity	NPC475147
0.6456	Remote Similarity	NPC67080
0.6456	Remote Similarity	NPC472121
0.6456	Remote Similarity	NPC118804
0.6453	Remote Similarity	NPC288110
0.645	Remote Similarity	NPC114468
0.6447	Remote Similarity	NPC330683
0.6447	Remote Similarity	NPC329567
0.6432	Remote Similarity	NPC158551
0.6429	Remote Similarity	NPC285254
0.6429	Remote Similarity	NPC138830
0.6423	Remote Similarity	NPC469722
0.6422	Remote Similarity	NPC148391
0.6415	Remote Similarity	NPC211713
0.6415	Remote Similarity	NPC129578
0.6415	Remote Similarity	NPC88378
0.6413	Remote Similarity	NPC17677
0.641	Remote Similarity	NPC182853
0.641	Remote Similarity	NPC87560
0.6407	Remote Similarity	NPC470482
0.6407	Remote Similarity	NPC470481
0.6406	Remote Similarity	NPC150308
0.6405	Remote Similarity	NPC329631
0.6402	Remote Similarity	NPC470480
0.64	Remote Similarity	NPC317567
0.6398	Remote Similarity	NPC76478
0.6398	Remote Similarity	NPC198503
0.6396	Remote Similarity	NPC470023
0.6395	Remote Similarity	NPC148183
0.6395	Remote Similarity	NPC152768
0.6393	Remote Similarity	NPC45389
0.6388	Remote Similarity	NPC133156
0.6375	Remote Similarity	NPC194740
0.6372	Remote Similarity	NPC476428
0.6368	Remote Similarity	NPC126556
0.6368	Remote Similarity	NPC473837
0.6364	Remote Similarity	NPC278887
0.636	Remote Similarity	NPC91868
0.636	Remote Similarity	NPC476500
0.636	Remote Similarity	NPC246140
0.636	Remote Similarity	NPC195787
0.636	Remote Similarity	NPC63971
0.6359	Remote Similarity	NPC469460
0.6356	Remote Similarity	NPC476069
0.6352	Remote Similarity	NPC2905
0.6349	Remote Similarity	NPC477397
0.634	Remote Similarity	NPC473041
0.634	Remote Similarity	NPC134702
0.634	Remote Similarity	NPC195120
0.6339	Remote Similarity	NPC193906
0.6339	Remote Similarity	NPC23080
0.6337	Remote Similarity	NPC473105
0.6335	Remote Similarity	NPC226708
0.6329	Remote Similarity	NPC118189
0.6326	Remote Similarity	NPC222524
0.6323	Remote Similarity	NPC477258
0.632	Remote Similarity	NPC14390
0.6318	Remote Similarity	NPC476444
0.6318	Remote Similarity	NPC19175

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 NPC470002 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	228
0.1-0.2	632
0.2-0.3	976
0.3-0.4	2083
0.4-0.5	3066
0.5-0.6	1994
0.6-0.7	171
0.7-0.8	0
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
0.6982	Remote Similarity	NPD5726	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD6198	Phase 1
0.6901	Remote Similarity	NPD6656	Clinical (unspecified phase)
0.69	Remote Similarity	NPD7556	Discontinued
0.6898	Remote Similarity	NPD4979	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD5937	Approved
0.683	Remote Similarity	NPD5914	Approved
0.6812	Remote Similarity	NPD5519	Discontinued
0.6802	Remote Similarity	NPD8161	Suspended
0.6784	Remote Similarity	NPD5617	Suspended
0.6758	Remote Similarity	NPD6874	Approved
0.6757	Remote Similarity	NPD3298	Approved
0.6697	Remote Similarity	NPD7566	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD6296	Discontinued
0.6682	Remote Similarity	NPD3297	Approved
0.6667	Remote Similarity	NPD7238	Clinical (unspecified phase)
0.6651	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6651	Remote Similarity	NPD6608	Clinical (unspecified phase)
0.665	Remote Similarity	NPD4986	Clinical (unspecified phase)
0.6624	Remote Similarity	NPD3912	Discontinued
0.6624	Remote Similarity	NPD4981	Phase 2
0.6603	Remote Similarity	NPD3446	Phase 1
0.6584	Remote Similarity	NPD6790	Phase 1
0.6578	Remote Similarity	NPD7174	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD2792	Approved
0.6567	Remote Similarity	NPD3437	Discontinued
0.656	Remote Similarity	NPD8492	Approved
0.656	Remote Similarity	NPD4740	Approved
0.6558	Remote Similarity	NPD3153	Approved
0.6558	Remote Similarity	NPD3154	Approved
0.6553	Remote Similarity	NPD3252	Approved
0.654	Remote Similarity	NPD3050	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD4946	Phase 2
0.6526	Remote Similarity	NPD6104	Discontinued
0.6511	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD3940	Clinical (unspecified phase)
0.6507	Remote Similarity	NPD1945	Phase 1
0.6488	Remote Similarity	NPD5967	Approved
0.6485	Remote Similarity	NPD5811	Approved
0.6476	Remote Similarity	NPD2898	Approved
0.646	Remote Similarity	NPD6250	Discontinued
0.6453	Remote Similarity	NPD2899	Discontinued
0.6453	Remote Similarity	NPD5496	Approved
0.6447	Remote Similarity	NPD2906	Approved
0.6447	Remote Similarity	NPD2907	Approved
0.6443	Remote Similarity	NPD8461	Discontinued
0.6441	Remote Similarity	NPD5195	Discontinued
0.6438	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.6438	Remote Similarity	NPD3949	Clinical (unspecified phase)
0.6435	Remote Similarity	NPD6567	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD7559	Phase 2
0.6422	Remote Similarity	NPD3398	Discontinued
0.641	Remote Similarity	NPD1926	Approved
0.6405	Remote Similarity	NPD6741	Clinical (unspecified phase)
0.64	Remote Similarity	NPD8367	Approved
0.64	Remote Similarity	NPD6525	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD5025	Approved
0.6394	Remote Similarity	NPD6862	Phase 2
0.6384	Remote Similarity	NPD7810	Phase 3
0.6384	Remote Similarity	NPD7811	Phase 3
0.638	Remote Similarity	NPD4466	Phase 1
0.6377	Remote Similarity	NPD4947	Clinical (unspecified phase)
0.6376	Remote Similarity	NPD3120	Approved
0.6376	Remote Similarity	NPD3119	Phase 1
0.6372	Remote Similarity	NPD5848	Clinical (unspecified phase)
0.6372	Remote Similarity	NPD956	Clinical (unspecified phase)
0.6372	Remote Similarity	NPD7626	Approved
0.6372	Remote Similarity	NPD7627	Approved
0.6368	Remote Similarity	NPD7019	Approved
0.6368	Remote Similarity	NPD7020	Approved
0.6364	Remote Similarity	NPD683	Approved
0.636	Remote Similarity	NPD7607	Clinical (unspecified phase)
0.6356	Remote Similarity	NPD1199	Approved
0.6356	Remote Similarity	NPD1200	Approved
0.6356	Remote Similarity	NPD7255	Clinical (unspecified phase)
0.6351	Remote Similarity	NPD4771	Phase 2
0.6349	Remote Similarity	NPD6199	Discontinued
0.6344	Remote Similarity	NPD3802	Phase 3
0.6344	Remote Similarity	NPD7497	Discontinued
0.6337	Remote Similarity	NPD4373	Phase 2
0.6336	Remote Similarity	NPD4492	Approved
0.6336	Remote Similarity	NPD7605	Discovery
0.6336	Remote Similarity	NPD4494	Approved
0.6326	Remote Similarity	NPD3823	Discontinued
0.6325	Remote Similarity	NPD7475	Clinical (unspecified phase)
0.6323	Remote Similarity	NPD4361	Phase 2
0.6323	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD2246	Approved
0.6321	Remote Similarity	NPD2248	Approved
0.6318	Remote Similarity	NPD4258	Approved
0.6318	Remote Similarity	NPD4259	Approved
0.6316	Remote Similarity	NPD4465	Phase 2
0.6316	Remote Similarity	NPD4467	Phase 2
0.6313	Remote Similarity	NPD7546	Discontinued
0.6309	Remote Similarity	NPD4455	Discontinued
0.6306	Remote Similarity	NPD4539	Phase 1
0.6304	Remote Similarity	NPD4082	Approved
0.6304	Remote Similarity	NPD6593	Clinical (unspecified phase)
0.6304	Remote Similarity	NPD7391	Discontinued
0.6303	Remote Similarity	NPD5186	Approved
0.6303	Remote Similarity	NPD5183	Approved
0.6288	Remote Similarity	NPD3507	Phase 2
0.6287	Remote Similarity	NPD5433	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD6037	Discontinued
0.6286	Remote Similarity	NPD3251	Approved
0.6284	Remote Similarity	NPD6021	Clinical (unspecified phase)
0.6282	Remote Similarity	NPD5293	Phase 2
0.6281	Remote Similarity	NPD4952	Phase 3
0.6276	Remote Similarity	NPD7278	Phase 2
0.6276	Remote Similarity	NPD7279	Phase 2
0.6275	Remote Similarity	NPD4613	Phase 2
0.6272	Remote Similarity	NPD7064	Clinical (unspecified phase)
0.627	Remote Similarity	NPD6625	Approved
0.6267	Remote Similarity	NPD7132	Clinical (unspecified phase)
0.6267	Remote Similarity	NPD1198	Approved
0.6266	Remote Similarity	NPD7268	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD2366	Approved
0.6262	Remote Similarity	NPD3004	Clinical (unspecified phase)
0.6261	Remote Similarity	NPD3601	Discontinued
0.6256	Remote Similarity	NPD6321	Discontinued
0.6256	Remote Similarity	NPD6457	Approved
0.6255	Remote Similarity	NPD6962	Phase 2
0.625	Remote Similarity	NPD8249	Clinical (unspecified phase)
0.625	Remote Similarity	NPD3925	Approved
0.625	Remote Similarity	NPD7318	Phase 3
0.6239	Remote Similarity	NPD4078	Clinical (unspecified phase)
0.6233	Remote Similarity	NPD3965	Phase 1
0.6233	Remote Similarity	NPD6020	Phase 2
0.6224	Remote Similarity	NPD7186	Phase 3
0.6223	Remote Similarity	NPD4493	Discontinued
0.6222	Remote Similarity	NPD5591	Approved
0.6222	Remote Similarity	NPD5515	Phase 2
0.6215	Remote Similarity	NPD5488	Discontinued
0.6211	Remote Similarity	NPD5879	Clinical (unspecified phase)
0.621	Remote Similarity	NPD7560	Approved
0.621	Remote Similarity	NPD7025	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD5594	Approved
0.6207	Remote Similarity	NPD5593	Approved
0.6205	Remote Similarity	NPD7256	Discontinued
0.6199	Remote Similarity	NPD1339	Discontinued
0.6198	Remote Similarity	NPD3259	Approved
0.6197	Remote Similarity	NPD3888	Discontinued
0.6197	Remote Similarity	NPD7301	Phase 3
0.6195	Remote Similarity	NPD814	Clinical (unspecified phase)
0.6193	Remote Similarity	NPD7190	Clinical (unspecified phase)
0.619	Remote Similarity	NPD7043	Discontinued
0.619	Remote Similarity	NPD4596	Phase 1
0.6188	Remote Similarity	NPD5968	Phase 3
0.6184	Remote Similarity	NPD5552	Discontinued
0.6184	Remote Similarity	NPD7476	Discontinued
0.618	Remote Similarity	NPD5860	Discontinued
0.6179	Remote Similarity	NPD2821	Approved
0.6178	Remote Similarity	NPD6722	Clinical (unspecified phase)
0.6175	Remote Similarity	NPD6293	Clinical (unspecified phase)
0.6174	Remote Similarity	NPD3946	Clinical (unspecified phase)
0.6174	Remote Similarity	NPD7891	Discontinued
0.6174	Remote Similarity	NPD1294	Discontinued
0.6172	Remote Similarity	NPD6063	Approved
0.6164	Remote Similarity	NPD4022	Approved
0.6164	Remote Similarity	NPD3472	Approved
0.6157	Remote Similarity	NPD8491	Approved
0.6154	Remote Similarity	NPD6844	Discontinued
0.6154	Remote Similarity	NPD7577	Discontinued
0.6154	Remote Similarity	NPD6793	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD7317	Phase 3
0.6151	Remote Similarity	NPD3783	Clinical (unspecified phase)
0.6148	Remote Similarity	NPD5801	Clinical (unspecified phase)
0.6147	Remote Similarity	NPD5637	Discontinued
0.6147	Remote Similarity	NPD6245	Phase 2
0.6146	Remote Similarity	NPD3641	Approved
0.6146	Remote Similarity	NPD3639	Approved
0.6146	Remote Similarity	NPD3640	Phase 3
0.6141	Remote Similarity	NPD7820	Phase 3
0.614	Remote Similarity	NPD2339	Phase 3
0.6132	Remote Similarity	NPD8469	Approved
0.6132	Remote Similarity	NPD710	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD3239	Clinical (unspecified phase)
0.6128	Remote Similarity	NPD7225	Discontinued
0.6126	Remote Similarity	NPD6040	Clinical (unspecified phase)
0.6126	Remote Similarity	NPD7291	Discontinued
0.6124	Remote Similarity	NPD6060	Clinical (unspecified phase)
0.6122	Remote Similarity	NPD8067	Phase 3
0.6121	Remote Similarity	NPD2215	Approved
0.6121	Remote Similarity	NPD2216	Approved
0.6116	Remote Similarity	NPD7821	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD3372	Discontinued
0.6111	Remote Similarity	NPD3893	Discontinued
0.6108	Remote Similarity	NPD160	Clinical (unspecified phase)
0.6104	Remote Similarity	NPD4040	Phase 1
0.6104	Remote Similarity	NPD4456	Clinical (unspecified phase)
0.6103	Remote Similarity	NPD3511	Discontinued
0.6101	Remote Similarity	NPD6654	Clinical (unspecified phase)
0.61	Remote Similarity	NPD6997	Phase 2
0.6099	Remote Similarity	NPD2843	Phase 2
0.6099	Remote Similarity	NPD2845	Phase 2
0.6098	Remote Similarity	NPD7031	Phase 1
0.6096	Remote Similarity	NPD5882	Clinical (unspecified phase)
0.6096	Remote Similarity	NPD5608	Approved
0.6096	Remote Similarity	NPD5609	Approved
0.6095	Remote Similarity	NPD5978	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