NPASS Compound

Structure

NPC474164 OpenBabel07101718322D 29 33 0 0 1 0 0 0 0 0999 V2000 -1.5962 -2.1100 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0292 2.4373 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0932 -0.7670 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7734 0.4240 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9563 -0.4158 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8253 1.2330 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9593 1.7330 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0248 2.8157 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0193 2.7111 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6473 0.5352 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8253 -1.7670 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2272 -0.2670 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9593 -1.2670 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3612 0.2330 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6913 -0.2670 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 -0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2872 -1.1590 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3601 1.6942 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.8253 0.2330 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6913 -1.2670 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.0932 1.2330 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6180 1.9021 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.2272 1.7330 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.0932 0.2330 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6691 0.7431 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.9593 -0.2670 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3612 1.2330 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 6.5573 -1.7670 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5 10 1 0 0 0 0 5 17 1 0 0 0 0 6 7 1 0 0 0 0 6 19 2 0 0 0 0 8 9 1 0 0 0 0 8 22 1 0 0 0 0 9 23 1 0 0 0 0 10 25 1 0 0 0 0 11 13 1 0 0 0 0 11 20 1 0 0 0 0 12 14 1 0 0 0 0 12 24 1 0 0 0 0 13 26 1 0 0 0 0 14 27 1 0 0 0 0 15 19 1 0 0 0 0 15 20 1 0 0 0 0 16 17 1 0 0 0 0 16 28 1 0 0 0 0 17 1 1 1 0 0 0 18 2 1 1 0 0 0 18 22 1 0 0 0 0 19 26 1 0 0 0 0 20 29 1 1 0 0 0 21 7 1 6 0 0 0 21 23 1 0 0 0 0 21 24 1 0 0 0 0 22 27 1 1 0 0 0 23 27 1 1 0 0 0 24 26 1 1 0 0 0 25 18 1 1 0 0 0 25 28 1 0 0 0 0 26 3 1 1 0 0 0 27 4 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	399.35
Volume:	449.916
LogP:	6.066
LogD:	4.886
LogS:	-5.026
# Rotatable Bonds:	2
TPSA:	32.26
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.562
Synthetic Accessibility Score:	4.683
Fsp3:	0.926
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.724
MDCK Permeability:	7.453614216501592e-06
Pgp-inhibitor:	0.969
Pgp-substrate:	0.967
Human Intestinal Absorption (HIA):	0.016
20% Bioavailability (F20%):	0.974
30% Bioavailability (F30%):	0.01

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.387
Plasma Protein Binding (PPB):	87.71443176269531%
Volume Distribution (VD):	0.913
Pgp-substrate:	2.8015642166137695%

ADMET: Metabolism

CYP1A2-inhibitor:	0.147
CYP1A2-substrate:	0.426
CYP2C19-inhibitor:	0.148
CYP2C19-substrate:	0.914
CYP2C9-inhibitor:	0.134
CYP2C9-substrate:	0.04
CYP2D6-inhibitor:	0.868
CYP2D6-substrate:	0.878
CYP3A4-inhibitor:	0.867
CYP3A4-substrate:	0.405

ADMET: Excretion

Clearance (CL):	14.451
Half-life (T1/2):	0.032

ADMET: Toxicity

hERG Blockers:	0.906
Human Hepatotoxicity (H-HT):	0.469
Drug-inuced Liver Injury (DILI):	0.355
AMES Toxicity:	0.075
Rat Oral Acute Toxicity:	0.787
Maximum Recommended Daily Dose:	0.929
Skin Sensitization:	0.962
Carcinogencity:	0.601
Eye Corrosion:	0.782
Eye Irritation:	0.035
Respiratory Toxicity:	0.966

Download Data

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

Natural Product: NPC474164

Natural Product ID:	NPC474164
*Common Name:**	Veramiline
IUPAC Name:	(3S,8S,9S,10R,13S,14S,17R)-10,13-dimethyl-17-[(1S)-1-[(2S,5S)-5-methylpiperidin-2-yl]ethyl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
Synonyms:	Veramiline
Standard InCHIKey:	SWTXHUUBYZNDAJ-BXTYSGRPSA-N
Standard InCHI:	InChI=1S/C27H45NO/c1-17-5-10-25(28-16-17)18(2)22-8-9-23-21-7-6-19-15-20(29)11-13-26(19,3)24(21)12-14-27(22,23)4/h6,17-18,20-25,28-29H,5,7-16H2,1-4H3/t17-,18-,20-,21-,22+,23-,24-,25-,26-,27+/m0/s1
SMILES:	CC1CCC(NC1)C(C)C2CCC3C2(CCC4C3CC=C5C4(CCC(C5)O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL463130
PubChem CID:	15559023
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0002724] Steroidal alkaloids [CHEMONTID:0002732] 22,26-epiminocholestanes

*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
NPO33146	eclipta alba	Species	n.a.	Eukaryota	n.a.	suriname rainforest1	n.a.	PMID[9784152]

☑ 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
Others	3

Activity Type	# Activity
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	IC12	=	3.0	ug ml-1	PMID[545647]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	IC12	=	4.0	ug ml-1	PMID[545647]

☑ 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 NPC474164 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	93
0.1-0.2	821
0.2-0.3	10876
0.3-0.4	15736
0.4-0.5	8123
0.5-0.6	5556
0.6-0.7	1292
0.7-0.8	183
0.8-0.85	10
0.85-0.9	5
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9574	High Similarity	NPC176012
0.8854	High Similarity	NPC91604
0.8812	High Similarity	NPC147835
0.8812	High Similarity	NPC85001
0.8812	High Similarity	NPC95920
0.8812	High Similarity	NPC253645
0.871	High Similarity	NPC84171
0.8384	Intermediate Similarity	NPC135799
0.837	Intermediate Similarity	NPC75810
0.8318	Intermediate Similarity	NPC28280
0.8318	Intermediate Similarity	NPC304646
0.8265	Intermediate Similarity	NPC289140
0.8252	Intermediate Similarity	NPC46981
0.8235	Intermediate Similarity	NPC212874
0.8173	Intermediate Similarity	NPC159367
0.8119	Intermediate Similarity	NPC118275
0.8081	Intermediate Similarity	NPC476903
0.8061	Intermediate Similarity	NPC280710
0.8061	Intermediate Similarity	NPC243985
0.8	Intermediate Similarity	NPC140300
0.7895	Intermediate Similarity	NPC296686
0.7876	Intermediate Similarity	NPC478138
0.7864	Intermediate Similarity	NPC50815
0.7826	Intermediate Similarity	NPC12035
0.7822	Intermediate Similarity	NPC240650
0.7798	Intermediate Similarity	NPC478137
0.7714	Intermediate Similarity	NPC475239
0.7692	Intermediate Similarity	NPC247060
0.7667	Intermediate Similarity	NPC162742
0.7667	Intermediate Similarity	NPC134847
0.7667	Intermediate Similarity	NPC285893
0.7667	Intermediate Similarity	NPC28657
0.7667	Intermediate Similarity	NPC136188
0.7667	Intermediate Similarity	NPC22105
0.7667	Intermediate Similarity	NPC230301
0.7667	Intermediate Similarity	NPC288035
0.7667	Intermediate Similarity	NPC304309
0.7624	Intermediate Similarity	NPC311164
0.7624	Intermediate Similarity	NPC272732
0.7619	Intermediate Similarity	NPC98765
0.7615	Intermediate Similarity	NPC79238
0.7607	Intermediate Similarity	NPC96010
0.7607	Intermediate Similarity	NPC317654
0.76	Intermediate Similarity	NPC93027
0.7582	Intermediate Similarity	NPC240604
0.7582	Intermediate Similarity	NPC113733
0.7582	Intermediate Similarity	NPC321016
0.7582	Intermediate Similarity	NPC321381
0.7582	Intermediate Similarity	NPC300324
0.7582	Intermediate Similarity	NPC107059
0.7524	Intermediate Similarity	NPC471083
0.75	Intermediate Similarity	NPC198968
0.75	Intermediate Similarity	NPC318495
0.75	Intermediate Similarity	NPC155986
0.75	Intermediate Similarity	NPC34019
0.75	Intermediate Similarity	NPC40488
0.7477	Intermediate Similarity	NPC477292
0.7477	Intermediate Similarity	NPC195841
0.7477	Intermediate Similarity	NPC233256
0.7473	Intermediate Similarity	NPC257347
0.7473	Intermediate Similarity	NPC141071
0.7473	Intermediate Similarity	NPC471723
0.7453	Intermediate Similarity	NPC293299
0.7453	Intermediate Similarity	NPC241879
0.7453	Intermediate Similarity	NPC45365
0.7451	Intermediate Similarity	NPC174117
0.7419	Intermediate Similarity	NPC474216
0.7419	Intermediate Similarity	NPC477522
0.7419	Intermediate Similarity	NPC307965
0.7419	Intermediate Similarity	NPC18603
0.7419	Intermediate Similarity	NPC473943
0.7419	Intermediate Similarity	NPC76931
0.7419	Intermediate Similarity	NPC87604
0.7391	Intermediate Similarity	NPC129165
0.7391	Intermediate Similarity	NPC189883
0.7391	Intermediate Similarity	NPC134330
0.7364	Intermediate Similarity	NPC472313
0.7355	Intermediate Similarity	NPC15249
0.7355	Intermediate Similarity	NPC25455
0.734	Intermediate Similarity	NPC47982
0.734	Intermediate Similarity	NPC109546
0.734	Intermediate Similarity	NPC28862
0.734	Intermediate Similarity	NPC84694
0.734	Intermediate Similarity	NPC328714
0.734	Intermediate Similarity	NPC143182
0.734	Intermediate Similarity	NPC81306
0.7304	Intermediate Similarity	NPC35037
0.7297	Intermediate Similarity	NPC474459
0.7295	Intermediate Similarity	NPC122819
0.7292	Intermediate Similarity	NPC5985
0.7282	Intermediate Similarity	NPC155985
0.7263	Intermediate Similarity	NPC209944
0.7263	Intermediate Similarity	NPC164840
0.7263	Intermediate Similarity	NPC26117
0.7263	Intermediate Similarity	NPC241290
0.7263	Intermediate Similarity	NPC234193
0.7248	Intermediate Similarity	NPC25340
0.7248	Intermediate Similarity	NPC476756
0.7248	Intermediate Similarity	NPC244982
0.7236	Intermediate Similarity	NPC147753
0.7236	Intermediate Similarity	NPC150057
0.7234	Intermediate Similarity	NPC275910
0.7232	Intermediate Similarity	NPC124358
0.7232	Intermediate Similarity	NPC474452
0.7204	Intermediate Similarity	NPC202642
0.7204	Intermediate Similarity	NPC244488
0.7204	Intermediate Similarity	NPC247325
0.7204	Intermediate Similarity	NPC470362
0.7204	Intermediate Similarity	NPC46160
0.7204	Intermediate Similarity	NPC96319
0.7204	Intermediate Similarity	NPC237460
0.7188	Intermediate Similarity	NPC474759
0.7188	Intermediate Similarity	NPC470383
0.7188	Intermediate Similarity	NPC47761
0.7188	Intermediate Similarity	NPC82986
0.7188	Intermediate Similarity	NPC118329
0.7188	Intermediate Similarity	NPC474683
0.7188	Intermediate Similarity	NPC152039
0.7188	Intermediate Similarity	NPC7505
0.7188	Intermediate Similarity	NPC23852
0.7188	Intermediate Similarity	NPC474731
0.7188	Intermediate Similarity	NPC474752
0.7188	Intermediate Similarity	NPC209620
0.7188	Intermediate Similarity	NPC474531
0.7188	Intermediate Similarity	NPC329782
0.7188	Intermediate Similarity	NPC264245
0.7158	Intermediate Similarity	NPC30986
0.7158	Intermediate Similarity	NPC1319
0.7158	Intermediate Similarity	NPC209430
0.7156	Intermediate Similarity	NPC86906
0.7143	Intermediate Similarity	NPC209802
0.713	Intermediate Similarity	NPC474583
0.7128	Intermediate Similarity	NPC214570
0.712	Intermediate Similarity	NPC297058
0.7115	Intermediate Similarity	NPC476261
0.7115	Intermediate Similarity	NPC119225
0.7115	Intermediate Similarity	NPC25033
0.7115	Intermediate Similarity	NPC470382
0.7115	Intermediate Similarity	NPC471635
0.7113	Intermediate Similarity	NPC1272
0.7113	Intermediate Similarity	NPC189972
0.7113	Intermediate Similarity	NPC470614
0.7113	Intermediate Similarity	NPC49964
0.7113	Intermediate Similarity	NPC472312
0.7113	Intermediate Similarity	NPC248886
0.7113	Intermediate Similarity	NPC101462
0.7113	Intermediate Similarity	NPC50964
0.71	Intermediate Similarity	NPC21035
0.7097	Intermediate Similarity	NPC118508
0.7097	Intermediate Similarity	NPC322353
0.7097	Intermediate Similarity	NPC121744
0.7087	Intermediate Similarity	NPC478140
0.7083	Intermediate Similarity	NPC94881
0.7083	Intermediate Similarity	NPC236112
0.7083	Intermediate Similarity	NPC48886
0.7083	Intermediate Similarity	NPC265275
0.7065	Intermediate Similarity	NPC471799
0.7065	Intermediate Similarity	NPC474140
0.7054	Intermediate Similarity	NPC287764
0.7053	Intermediate Similarity	NPC85346
0.7053	Intermediate Similarity	NPC138621
0.7053	Intermediate Similarity	NPC285761
0.7053	Intermediate Similarity	NPC302041
0.7053	Intermediate Similarity	NPC205455
0.7053	Intermediate Similarity	NPC167037
0.7053	Intermediate Similarity	NPC186191
0.7053	Intermediate Similarity	NPC65897
0.7053	Intermediate Similarity	NPC244385
0.7053	Intermediate Similarity	NPC477514
0.7053	Intermediate Similarity	NPC6978
0.7041	Intermediate Similarity	NPC474634
0.7041	Intermediate Similarity	NPC317458
0.7041	Intermediate Similarity	NPC246956
0.7041	Intermediate Similarity	NPC475789
0.7021	Intermediate Similarity	NPC106364
0.7021	Intermediate Similarity	NPC73875
0.7009	Intermediate Similarity	NPC239768
0.7009	Intermediate Similarity	NPC128698
0.7008	Intermediate Similarity	NPC287885
0.7	Intermediate Similarity	NPC24277
0.7	Intermediate Similarity	NPC160209
0.7	Intermediate Similarity	NPC55462
0.7	Intermediate Similarity	NPC208999
0.6992	Remote Similarity	NPC478139
0.6989	Remote Similarity	NPC469533
0.6989	Remote Similarity	NPC100334
0.6989	Remote Similarity	NPC469593
0.6989	Remote Similarity	NPC471797
0.6989	Remote Similarity	NPC469534
0.6979	Remote Similarity	NPC80530
0.6979	Remote Similarity	NPC273410
0.697	Remote Similarity	NPC221758
0.697	Remote Similarity	NPC185568
0.697	Remote Similarity	NPC205845
0.697	Remote Similarity	NPC33913
0.697	Remote Similarity	NPC124172
0.697	Remote Similarity	NPC472265
0.697	Remote Similarity	NPC59453
0.6967	Remote Similarity	NPC478136
0.6939	Remote Similarity	NPC30166

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 NPC474164 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	95
0.1-0.2	468
0.2-0.3	3360
0.3-0.4	3635
0.4-0.5	1161
0.5-0.6	345
0.6-0.7	76
0.7-0.8	10
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
0.7667	Intermediate Similarity	NPD7339	Approved
0.7667	Intermediate Similarity	NPD6942	Approved
0.7295	Intermediate Similarity	NPD8449	Approved
0.7236	Intermediate Similarity	NPD8450	Suspended
0.7204	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD7337	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD7336	Phase 2
0.708	Intermediate Similarity	NPD7335	Phase 2
0.697	Remote Similarity	NPD4786	Approved
0.6907	Remote Similarity	NPD7525	Registered
0.6847	Remote Similarity	NPD7333	Discontinued
0.6822	Remote Similarity	NPD7920	Phase 3
0.6822	Remote Similarity	NPD7919	Phase 3
0.6809	Remote Similarity	NPD4784	Approved
0.6809	Remote Similarity	NPD6924	Approved
0.6809	Remote Similarity	NPD4785	Approved
0.6809	Remote Similarity	NPD6926	Approved
0.6774	Remote Similarity	NPD7150	Approved
0.6774	Remote Similarity	NPD4243	Approved
0.6774	Remote Similarity	NPD7151	Approved
0.6774	Remote Similarity	NPD7152	Approved
0.6768	Remote Similarity	NPD3667	Approved
0.6759	Remote Similarity	NPD8088	Phase 1
0.6739	Remote Similarity	NPD6923	Approved
0.6739	Remote Similarity	NPD6922	Approved
0.6667	Remote Similarity	NPD6933	Approved
0.6667	Remote Similarity	NPD7144	Approved
0.6667	Remote Similarity	NPD7143	Approved
0.6633	Remote Similarity	NPD7645	Phase 2
0.6602	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD8308	Discontinued
0.6476	Remote Similarity	NPD5328	Approved
0.6465	Remote Similarity	NPD6929	Approved
0.64	Remote Similarity	NPD4748	Discontinued
0.64	Remote Similarity	NPD6930	Phase 2
0.64	Remote Similarity	NPD6931	Approved
0.6392	Remote Similarity	NPD5275	Approved
0.6392	Remote Similarity	NPD4190	Phase 3
0.6389	Remote Similarity	NPD5771	Approved
0.6355	Remote Similarity	NPD6079	Approved
0.6346	Remote Similarity	NPD3618	Phase 1
0.6311	Remote Similarity	NPD3666	Approved
0.6311	Remote Similarity	NPD3665	Phase 1
0.6311	Remote Similarity	NPD3133	Approved
0.6296	Remote Similarity	NPD6399	Phase 3
0.6263	Remote Similarity	NPD5776	Phase 2
0.6263	Remote Similarity	NPD6932	Approved
0.6263	Remote Similarity	NPD6925	Approved
0.6238	Remote Similarity	NPD7509	Discontinued
0.6226	Remote Similarity	NPD4723	Approved
0.6226	Remote Similarity	NPD4722	Approved
0.6214	Remote Similarity	NPD6695	Phase 3
0.62	Remote Similarity	NPD7145	Approved
0.6198	Remote Similarity	NPD7754	Approved
0.6198	Remote Similarity	NPD7755	Approved
0.6187	Remote Similarity	NPD8131	Suspended
0.6154	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD3668	Phase 3
0.6148	Remote Similarity	NPD4032	Approved
0.6148	Remote Similarity	NPD4031	Approved
0.6147	Remote Similarity	NPD4202	Approved
0.6139	Remote Similarity	NPD6683	Phase 2
0.6139	Remote Similarity	NPD4195	Approved
0.6129	Remote Similarity	NPD2227	Clinical (unspecified phase)
0.6121	Remote Similarity	NPD6920	Discontinued
0.6095	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6095	Remote Similarity	NPD6893	Approved
0.6082	Remote Similarity	NPD5365	Phase 2
0.608	Remote Similarity	NPD6908	Approved
0.608	Remote Similarity	NPD6909	Approved
0.6078	Remote Similarity	NPD7514	Phase 3
0.604	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6038	Remote Similarity	NPD5279	Phase 3
0.6019	Remote Similarity	NPD6902	Approved
0.6019	Remote Similarity	NPD4753	Phase 2
0.6017	Remote Similarity	NPD6415	Discontinued
0.5982	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5982	Remote Similarity	NPD4697	Phase 3
0.5982	Remote Similarity	NPD5221	Approved
0.5982	Remote Similarity	NPD5222	Approved
0.5981	Remote Similarity	NPD7524	Approved
0.5981	Remote Similarity	NPD7750	Discontinued
0.5962	Remote Similarity	NPD4223	Phase 3
0.5962	Remote Similarity	NPD4221	Approved
0.5954	Remote Similarity	NPD7751	Phase 1
0.5952	Remote Similarity	NPD1710	Approved
0.5943	Remote Similarity	NPD5329	Approved
0.5932	Remote Similarity	NPD7646	Clinical (unspecified phase)
0.5929	Remote Similarity	NPD4755	Approved
0.5929	Remote Similarity	NPD5173	Approved
0.5929	Remote Similarity	NPD3638	Discontinued
0.5922	Remote Similarity	NPD7332	Phase 2
0.592	Remote Similarity	NPD7519	Approved
0.592	Remote Similarity	NPD7517	Approved
0.592	Remote Similarity	NPD7518	Approved
0.592	Remote Similarity	NPD7522	Discontinued
0.5909	Remote Similarity	NPD7515	Phase 2
0.5906	Remote Similarity	NPD7725	Approved
0.59	Remote Similarity	NPD8264	Approved
0.5865	Remote Similarity	NPD6898	Phase 1
0.5862	Remote Similarity	NPD4719	Phase 2
0.5859	Remote Similarity	NPD7122	Discontinued
0.5849	Remote Similarity	NPD4197	Approved
0.5826	Remote Similarity	NPD5286	Approved
0.5826	Remote Similarity	NPD4696	Approved
0.5826	Remote Similarity	NPD5285	Approved
0.5826	Remote Similarity	NPD4700	Approved
0.582	Remote Similarity	NPD8078	Approved
0.582	Remote Similarity	NPD8077	Approved
0.5816	Remote Similarity	NPD6938	Clinical (unspecified phase)
0.5816	Remote Similarity	NPD6939	Phase 2
0.5789	Remote Similarity	NPD6084	Phase 2
0.5789	Remote Similarity	NPD6083	Phase 2
0.578	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5776	Remote Similarity	NPD5223	Approved
0.5776	Remote Similarity	NPD4159	Approved
0.5766	Remote Similarity	NPD7087	Discontinued
0.5755	Remote Similarity	NPD4788	Approved
0.5752	Remote Similarity	NPD7991	Discontinued
0.5752	Remote Similarity	NPD5210	Approved
0.5752	Remote Similarity	NPD4629	Approved
0.5748	Remote Similarity	NPD7147	Phase 3
0.5748	Remote Similarity	NPD7148	Clinical (unspecified phase)
0.5741	Remote Similarity	NPD4138	Approved
0.5741	Remote Similarity	NPD5330	Approved
0.5741	Remote Similarity	NPD7521	Approved
0.5741	Remote Similarity	NPD4693	Phase 3
0.5741	Remote Similarity	NPD4690	Approved
0.5741	Remote Similarity	NPD5205	Approved
0.5741	Remote Similarity	NPD7334	Approved
0.5741	Remote Similarity	NPD6409	Approved
0.5741	Remote Similarity	NPD7146	Approved
0.5741	Remote Similarity	NPD4689	Approved
0.5741	Remote Similarity	NPD6684	Approved
0.5741	Remote Similarity	NPD4688	Approved
0.5739	Remote Similarity	NPD7638	Approved
0.5739	Remote Similarity	NPD5290	Discontinued
0.5727	Remote Similarity	NPD6051	Approved
0.5726	Remote Similarity	NPD5226	Approved
0.5726	Remote Similarity	NPD5224	Approved
0.5726	Remote Similarity	NPD5225	Approved
0.5726	Remote Similarity	NPD5211	Phase 2
0.5726	Remote Similarity	NPD4633	Approved
0.5724	Remote Similarity	NPD3645	Discontinued
0.5714	Remote Similarity	NPD7128	Approved
0.5714	Remote Similarity	NPD6675	Approved
0.5714	Remote Similarity	NPD5739	Approved
0.5714	Remote Similarity	NPD6402	Approved
0.5714	Remote Similarity	NPD6914	Discontinued
0.5714	Remote Similarity	NPD6640	Phase 3
0.5691	Remote Similarity	NPD6429	Approved
0.5691	Remote Similarity	NPD6430	Approved
0.569	Remote Similarity	NPD6404	Discontinued
0.569	Remote Similarity	NPD7640	Approved
0.569	Remote Similarity	NPD7639	Approved
0.5686	Remote Similarity	NPD1346	Approved
0.5678	Remote Similarity	NPD5174	Approved
0.5678	Remote Similarity	NPD4754	Approved
0.5678	Remote Similarity	NPD5175	Approved
0.5676	Remote Similarity	NPD4001	Clinical (unspecified phase)
0.5676	Remote Similarity	NPD4096	Approved
0.5667	Remote Similarity	NPD6412	Phase 2
0.5664	Remote Similarity	NPD7748	Approved
0.5664	Remote Similarity	NPD5707	Approved
0.5664	Remote Similarity	NPD5769	Clinical (unspecified phase)
0.5636	Remote Similarity	NPD6903	Approved
0.5636	Remote Similarity	NPD5737	Approved
0.5636	Remote Similarity	NPD6672	Approved
0.563	Remote Similarity	NPD5141	Approved
0.5625	Remote Similarity	NPD8035	Phase 2
0.5625	Remote Similarity	NPD2106	Clinical (unspecified phase)
0.5625	Remote Similarity	NPD8034	Phase 2
0.562	Remote Similarity	NPD6899	Approved
0.562	Remote Similarity	NPD7320	Approved
0.562	Remote Similarity	NPD6881	Approved
0.5612	Remote Similarity	NPD6705	Phase 1

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