NPASS Compound

Structure

NPC182549 OpenBabel07101718322D 28 28 0 0 1 0 0 0 0 0999 V2000 -3.4641 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 6.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 6.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 6.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 4.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 3.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 5.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 4 1 0 0 0 0 4 17 1 0 0 0 0 5 7 2 0 0 0 0 5 8 1 0 0 0 0 6 9 2 0 0 0 0 6 10 1 0 0 0 0 7 11 1 0 0 0 0 8 12 2 0 0 0 0 9 13 1 0 0 0 0 10 14 2 0 0 0 0 11 19 2 0 0 0 0 12 19 1 0 0 0 0 14 21 1 0 0 0 0 15 16 2 0 0 0 0 15 19 1 0 0 0 0 16 22 1 0 0 0 0 17 2 1 1 0 0 0 17 23 1 0 0 0 0 18 3 1 6 0 0 0 18 20 1 0 0 0 0 18 23 1 0 0 0 0 20 13 1 1 0 0 0 20 28 1 0 0 0 0 21 24 2 0 0 0 0 21 25 1 0 0 0 0 22 26 2 0 0 0 0 22 28 1 0 0 0 0 23 27 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	385.23
Volume:	422.874
LogP:	3.316
LogD:	3.496
LogS:	-3.857
# Rotatable Bonds:	12
TPSA:	89.62
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	1
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.346
Synthetic Accessibility Score:	4.096
Fsp3:	0.391
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.932
MDCK Permeability:	1.726999835227616e-05
Pgp-inhibitor:	0.016
Pgp-substrate:	0.532
Human Intestinal Absorption (HIA):	0.018
20% Bioavailability (F20%):	0.105
30% Bioavailability (F30%):	0.046

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.993
Plasma Protein Binding (PPB):	97.43257141113281%
Volume Distribution (VD):	0.689
Pgp-substrate:	2.985532760620117%

ADMET: Metabolism

CYP1A2-inhibitor:	0.74
CYP1A2-substrate:	0.067
CYP2C19-inhibitor:	0.067
CYP2C19-substrate:	0.1
CYP2C9-inhibitor:	0.456
CYP2C9-substrate:	0.402
CYP2D6-inhibitor:	0.033
CYP2D6-substrate:	0.156
CYP3A4-inhibitor:	0.705
CYP3A4-substrate:	0.262

ADMET: Excretion

Clearance (CL):	6.845
Half-life (T1/2):	0.498

ADMET: Toxicity

hERG Blockers:	0.782
Human Hepatotoxicity (H-HT):	0.436
Drug-inuced Liver Injury (DILI):	0.038
AMES Toxicity:	0.353
Rat Oral Acute Toxicity:	0.274
Maximum Recommended Daily Dose:	0.923
Skin Sensitization:	0.954
Carcinogencity:	0.302
Eye Corrosion:	0.004
Eye Irritation:	0.037
Respiratory Toxicity:	0.896

Download Data

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

Natural Product: NPC182549

Natural Product ID:	NPC182549
*Common Name:**	Basiliskamide B
IUPAC Name:	[(3R,4S,5S,6R,8E,10Z)-12-amino-4-hydroxy-3,5-dimethyl-12-oxododeca-8,10-dien-6-yl] (E)-3-phenylprop-2-enoate
Synonyms:
Standard InCHIKey:	HCZNVGHFFHRIFM-HXKCHMFGSA-N
Standard InCHI:	InChI=1S/C23H31NO4/c1-4-17(2)23(27)18(3)20(13-9-6-10-14-21(24)25)28-22(26)16-15-19-11-7-5-8-12-19/h5-12,14-18,20,23,27H,4,13H2,1-3H3,(H2,24,25)/b9-6+,14-10-,16-15+/t17-,18-,20-,23+/m1/s1
SMILES:	CC[C@H]([C@@H]([C@@H]([C@H](OC(=O)/C=C/c1ccccc1)C/C=C/C=CC(=N)O)C)O)C
Synthetic Gene Cluster:	BGC0000172;
ChEMBL Identifier:	CHEMBL484461
PubChem CID:	9908152
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000476] Cinnamic acids and derivatives [CHEMONTID:0003480] Cinnamic acid esters

*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
NPO33156	bacillus laterosporus	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[12398541]

☑ 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	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT87	Organism	Aspergillus fumigatus	Aspergillus fumigatus	MIC	=	5.0	ug.mL-1	PMID[515866]
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	3.1	ug.mL-1	PMID[515866]

☑ 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 NPC182549 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	94
0.1-0.2	567
0.2-0.3	2698
0.3-0.4	7551
0.4-0.5	16823
0.5-0.6	12911
0.6-0.7	1907
0.7-0.8	137
0.8-0.85	6
0.85-0.9	0
0.9-0.95	0
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC114741
0.9804	High Similarity	NPC323007
0.8165	Intermediate Similarity	NPC136962
0.8165	Intermediate Similarity	NPC477251
0.8	Intermediate Similarity	NPC472316
0.8	Intermediate Similarity	NPC474376
0.8	Intermediate Similarity	NPC475203
0.8	Intermediate Similarity	NPC472315
0.7982	Intermediate Similarity	NPC242913
0.7982	Intermediate Similarity	NPC280616
0.7982	Intermediate Similarity	NPC171831
0.7838	Intermediate Similarity	NPC37115
0.781	Intermediate Similarity	NPC23453
0.7807	Intermediate Similarity	NPC234376
0.7768	Intermediate Similarity	NPC20485
0.7739	Intermediate Similarity	NPC265002
0.7727	Intermediate Similarity	NPC91820
0.7727	Intermediate Similarity	NPC82426
0.7686	Intermediate Similarity	NPC160493
0.7627	Intermediate Similarity	NPC470820
0.7619	Intermediate Similarity	NPC472319
0.7611	Intermediate Similarity	NPC277788
0.7586	Intermediate Similarity	NPC273814
0.7565	Intermediate Similarity	NPC477247
0.7524	Intermediate Similarity	NPC240108
0.7524	Intermediate Similarity	NPC213156
0.7523	Intermediate Similarity	NPC154517
0.7521	Intermediate Similarity	NPC190663
0.7521	Intermediate Similarity	NPC80150
0.75	Intermediate Similarity	NPC139946
0.75	Intermediate Similarity	NPC30361
0.75	Intermediate Similarity	NPC303245
0.75	Intermediate Similarity	NPC89950
0.75	Intermediate Similarity	NPC477250
0.7455	Intermediate Similarity	NPC80115
0.7434	Intermediate Similarity	NPC472919
0.7414	Intermediate Similarity	NPC476003
0.7411	Intermediate Similarity	NPC234305
0.7404	Intermediate Similarity	NPC286608
0.7404	Intermediate Similarity	NPC169050
0.7398	Intermediate Similarity	NPC475328
0.7391	Intermediate Similarity	NPC184633
0.7368	Intermediate Similarity	NPC51174
0.7364	Intermediate Similarity	NPC135951
0.7353	Intermediate Similarity	NPC127491
0.7353	Intermediate Similarity	NPC308619
0.7353	Intermediate Similarity	NPC324835
0.735	Intermediate Similarity	NPC185840
0.735	Intermediate Similarity	NPC470825
0.7345	Intermediate Similarity	NPC85977
0.7333	Intermediate Similarity	NPC304760
0.7304	Intermediate Similarity	NPC475465
0.7304	Intermediate Similarity	NPC472314
0.73	Intermediate Similarity	NPC78517
0.73	Intermediate Similarity	NPC167577
0.7297	Intermediate Similarity	NPC472318
0.7297	Intermediate Similarity	NPC98911
0.7288	Intermediate Similarity	NPC477246
0.7288	Intermediate Similarity	NPC477245
0.7273	Intermediate Similarity	NPC122117
0.7265	Intermediate Similarity	NPC133308
0.7265	Intermediate Similarity	NPC63345
0.7265	Intermediate Similarity	NPC183700
0.7265	Intermediate Similarity	NPC43584
0.7264	Intermediate Similarity	NPC173443
0.7257	Intermediate Similarity	NPC304638
0.725	Intermediate Similarity	NPC235421
0.7241	Intermediate Similarity	NPC469636
0.7238	Intermediate Similarity	NPC96625
0.7236	Intermediate Similarity	NPC476183
0.7232	Intermediate Similarity	NPC469481
0.7227	Intermediate Similarity	NPC474641
0.7227	Intermediate Similarity	NPC153053
0.7222	Intermediate Similarity	NPC77273
0.7212	Intermediate Similarity	NPC99482
0.7212	Intermediate Similarity	NPC475710
0.7207	Intermediate Similarity	NPC179411
0.72	Intermediate Similarity	NPC176228
0.7184	Intermediate Similarity	NPC243289
0.7184	Intermediate Similarity	NPC208183
0.7177	Intermediate Similarity	NPC476281
0.7177	Intermediate Similarity	NPC476184
0.7165	Intermediate Similarity	NPC45821
0.7155	Intermediate Similarity	NPC47536
0.7155	Intermediate Similarity	NPC260952
0.7143	Intermediate Similarity	NPC470815
0.7143	Intermediate Similarity	NPC140118
0.7143	Intermediate Similarity	NPC12881
0.7143	Intermediate Similarity	NPC472373
0.713	Intermediate Similarity	NPC119631
0.7129	Intermediate Similarity	NPC469894
0.7117	Intermediate Similarity	NPC289201
0.7115	Intermediate Similarity	NPC304538
0.7111	Intermediate Similarity	NPC111586
0.7111	Intermediate Similarity	NPC108852
0.7111	Intermediate Similarity	NPC261709
0.7109	Intermediate Similarity	NPC477365
0.7105	Intermediate Similarity	NPC474365
0.7105	Intermediate Similarity	NPC301943
0.7103	Intermediate Similarity	NPC220893
0.71	Intermediate Similarity	NPC287790
0.71	Intermediate Similarity	NPC3672
0.7097	Intermediate Similarity	NPC474223
0.7097	Intermediate Similarity	NPC475827
0.7094	Intermediate Similarity	NPC469511
0.7094	Intermediate Similarity	NPC40178
0.7091	Intermediate Similarity	NPC58674
0.7087	Intermediate Similarity	NPC474532
0.7087	Intermediate Similarity	NPC103387
0.7087	Intermediate Similarity	NPC471758
0.7083	Intermediate Similarity	NPC87069
0.7083	Intermediate Similarity	NPC474363
0.708	Intermediate Similarity	NPC253746
0.7073	Intermediate Similarity	NPC309434
0.7073	Intermediate Similarity	NPC310467
0.7063	Intermediate Similarity	NPC476278
0.7063	Intermediate Similarity	NPC12016
0.7059	Intermediate Similarity	NPC321852
0.7059	Intermediate Similarity	NPC158282
0.7054	Intermediate Similarity	NPC58061
0.7054	Intermediate Similarity	NPC230331
0.7054	Intermediate Similarity	NPC317280
0.7054	Intermediate Similarity	NPC329387
0.7054	Intermediate Similarity	NPC477370
0.7049	Intermediate Similarity	NPC281277
0.7049	Intermediate Similarity	NPC123559
0.7048	Intermediate Similarity	NPC53299
0.7048	Intermediate Similarity	NPC58616
0.7045	Intermediate Similarity	NPC90693
0.7045	Intermediate Similarity	NPC64897
0.7043	Intermediate Similarity	NPC472222
0.7043	Intermediate Similarity	NPC472221
0.7043	Intermediate Similarity	NPC19136
0.7037	Intermediate Similarity	NPC185501
0.7034	Intermediate Similarity	NPC471954
0.7034	Intermediate Similarity	NPC75272
0.7031	Intermediate Similarity	NPC477363
0.7031	Intermediate Similarity	NPC275576
0.7031	Intermediate Similarity	NPC477366
0.7025	Intermediate Similarity	NPC41851
0.7019	Intermediate Similarity	NPC270507
0.7018	Intermediate Similarity	NPC94343
0.7008	Intermediate Similarity	NPC477362
0.7008	Intermediate Similarity	NPC476241
0.7008	Intermediate Similarity	NPC471466
0.7008	Intermediate Similarity	NPC476260
0.7	Intermediate Similarity	NPC175393
0.7	Intermediate Similarity	NPC272524
0.7	Intermediate Similarity	NPC128368
0.6992	Remote Similarity	NPC169328
0.6991	Remote Similarity	NPC146351
0.6991	Remote Similarity	NPC171843
0.6984	Remote Similarity	NPC474862
0.6983	Remote Similarity	NPC127676
0.6983	Remote Similarity	NPC321670
0.6977	Remote Similarity	NPC169913
0.6975	Remote Similarity	NPC260818
0.6967	Remote Similarity	NPC474967
0.6967	Remote Similarity	NPC476476
0.6967	Remote Similarity	NPC233669
0.6961	Remote Similarity	NPC170484
0.696	Remote Similarity	NPC477061
0.696	Remote Similarity	NPC45777
0.6957	Remote Similarity	NPC160382
0.6953	Remote Similarity	NPC476179
0.6953	Remote Similarity	NPC476125
0.6953	Remote Similarity	NPC284022
0.6952	Remote Similarity	NPC44546
0.6949	Remote Similarity	NPC206341
0.6949	Remote Similarity	NPC281604
0.6942	Remote Similarity	NPC474544
0.6942	Remote Similarity	NPC307651
0.6942	Remote Similarity	NPC1986
0.6935	Remote Similarity	NPC203124
0.6935	Remote Similarity	NPC314992
0.693	Remote Similarity	NPC469457
0.6929	Remote Similarity	NPC474254
0.6929	Remote Similarity	NPC477151
0.6929	Remote Similarity	NPC325301
0.6929	Remote Similarity	NPC132518
0.6929	Remote Similarity	NPC474159
0.6929	Remote Similarity	NPC327070
0.6923	Remote Similarity	NPC323103
0.6923	Remote Similarity	NPC101372
0.6923	Remote Similarity	NPC283012
0.6923	Remote Similarity	NPC329319
0.6923	Remote Similarity	NPC92623
0.6923	Remote Similarity	NPC14326
0.6923	Remote Similarity	NPC326447
0.6923	Remote Similarity	NPC99394
0.6923	Remote Similarity	NPC191215
0.6923	Remote Similarity	NPC99240
0.6923	Remote Similarity	NPC274089
0.6923	Remote Similarity	NPC73637
0.6923	Remote Similarity	NPC121478
0.6923	Remote Similarity	NPC135464
0.6923	Remote Similarity	NPC475199
0.6923	Remote Similarity	NPC103326
0.6923	Remote Similarity	NPC87299
0.6917	Remote Similarity	NPC270699

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 NPC182549 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	99
0.1-0.2	429
0.2-0.3	1058
0.3-0.4	2762
0.4-0.5	2864
0.5-0.6	1645
0.6-0.7	284
0.7-0.8	9
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
0.789	Intermediate Similarity	NPD6647	Phase 2
0.7685	Intermediate Similarity	NPD5926	Approved
0.7404	Intermediate Similarity	NPD1282	Approved
0.7304	Intermediate Similarity	NPD6406	Approved
0.7281	Intermediate Similarity	NPD5048	Discontinued
0.7264	Intermediate Similarity	NPD689	Discontinued
0.7257	Intermediate Similarity	NPD5738	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD5909	Discontinued
0.717	Intermediate Similarity	NPD531	Approved
0.7156	Intermediate Similarity	NPD1066	Discontinued
0.712	Intermediate Similarity	NPD4480	Approved
0.7069	Intermediate Similarity	NPD6685	Approved
0.7049	Intermediate Similarity	NPD694	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD2067	Discontinued
0.7	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD6287	Discontinued
0.6975	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD6010	Discontinued
0.6937	Remote Similarity	NPD4814	Discontinued
0.6935	Remote Similarity	NPD2218	Phase 2
0.6935	Remote Similarity	NPD2217	Approved
0.6929	Remote Similarity	NPD6637	Approved
0.6923	Remote Similarity	NPD467	Phase 1
0.6923	Remote Similarity	NPD3134	Approved
0.6906	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.69	Remote Similarity	NPD9716	Approved
0.6887	Remote Similarity	NPD5734	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD2629	Approved
0.6857	Remote Similarity	NPD3971	Phase 1
0.6852	Remote Similarity	NPD1101	Approved
0.6847	Remote Similarity	NPD3718	Approved
0.6847	Remote Similarity	NPD3719	Approved
0.6842	Remote Similarity	NPD2066	Phase 3
0.6818	Remote Similarity	NPD3136	Phase 2
0.6818	Remote Similarity	NPD530	Approved
0.6815	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.681	Remote Similarity	NPD5765	Approved
0.6807	Remote Similarity	NPD2182	Approved
0.6803	Remote Similarity	NPD2650	Approved
0.6803	Remote Similarity	NPD2652	Approved
0.6777	Remote Similarity	NPD6912	Phase 3
0.6777	Remote Similarity	NPD969	Suspended
0.6757	Remote Similarity	NPD159	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD9609	Approved
0.6754	Remote Similarity	NPD9495	Approved
0.6754	Remote Similarity	NPD9611	Approved
0.6754	Remote Similarity	NPD9612	Approved
0.675	Remote Similarity	NPD5237	Approved
0.675	Remote Similarity	NPD5239	Approved
0.675	Remote Similarity	NPD5240	Approved
0.675	Remote Similarity	NPD9713	Approved
0.675	Remote Similarity	NPD5236	Approved
0.675	Remote Similarity	NPD5235	Approved
0.6727	Remote Similarity	NPD3672	Approved
0.6727	Remote Similarity	NPD3673	Approved
0.6723	Remote Similarity	NPD1358	Approved
0.6718	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD1067	Discontinued
0.6696	Remote Similarity	NPD9712	Approved
0.6694	Remote Similarity	NPD2201	Approved
0.6694	Remote Similarity	NPD4198	Discontinued
0.6693	Remote Similarity	NPD5305	Approved
0.6693	Remote Similarity	NPD5306	Approved
0.6692	Remote Similarity	NPD5454	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6642	Remote Similarity	NPD1048	Approved
0.664	Remote Similarity	NPD5291	Approved
0.664	Remote Similarity	NPD5292	Approved
0.6639	Remote Similarity	NPD2551	Approved
0.6639	Remote Similarity	NPD5706	Approved
0.6639	Remote Similarity	NPD2559	Approved
0.6639	Remote Similarity	NPD5705	Approved
0.6639	Remote Similarity	NPD5704	Approved
0.6638	Remote Similarity	NPD2558	Approved
0.6638	Remote Similarity	NPD2555	Approved
0.6638	Remote Similarity	NPD2553	Approved
0.6638	Remote Similarity	NPD2549	Approved
0.6638	Remote Similarity	NPD2550	Approved
0.6638	Remote Similarity	NPD2552	Approved
0.6636	Remote Similarity	NPD5346	Phase 2
0.6636	Remote Similarity	NPD5347	Phase 2
0.6636	Remote Similarity	NPD800	Approved
0.6615	Remote Similarity	NPD3685	Discontinued
0.6614	Remote Similarity	NPD5981	Approved
0.6614	Remote Similarity	NPD4209	Clinical (unspecified phase)
0.6613	Remote Similarity	NPD690	Clinical (unspecified phase)
0.661	Remote Similarity	NPD1237	Approved
0.6609	Remote Similarity	NPD9711	Approved
0.6609	Remote Similarity	NPD9710	Approved
0.6606	Remote Similarity	NPD9538	Approved
0.6589	Remote Similarity	NPD2609	Approved
0.6589	Remote Similarity	NPD2608	Approved
0.6589	Remote Similarity	NPD4217	Approved
0.6589	Remote Similarity	NPD4806	Approved
0.6589	Remote Similarity	NPD3131	Approved
0.6589	Remote Similarity	NPD4216	Approved
0.6589	Remote Similarity	NPD4807	Approved
0.6589	Remote Similarity	NPD2612	Approved
0.6589	Remote Similarity	NPD4215	Approved
0.6589	Remote Similarity	NPD2611	Approved
0.6589	Remote Similarity	NPD4218	Approved
0.6589	Remote Similarity	NPD3132	Approved
0.6589	Remote Similarity	NPD2610	Approved
0.6585	Remote Similarity	NPD821	Approved
0.6583	Remote Similarity	NPD9532	Phase 3
0.6581	Remote Similarity	NPD4189	Approved
0.6581	Remote Similarity	NPD4188	Approved
0.6577	Remote Similarity	NPD1090	Approved
0.6577	Remote Similarity	NPD1086	Approved
0.6577	Remote Similarity	NPD1089	Approved
0.6567	Remote Similarity	NPD4738	Phase 2
0.6567	Remote Similarity	NPD6919	Clinical (unspecified phase)
0.6565	Remote Similarity	NPD2198	Approved
0.6565	Remote Similarity	NPD2199	Approved
0.6555	Remote Similarity	NPD1040	Phase 2
0.6552	Remote Similarity	NPD1238	Approved
0.6549	Remote Similarity	NPD1409	Phase 3
0.6544	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6544	Remote Similarity	NPD2203	Discontinued
0.6538	Remote Similarity	NPD5108	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD7741	Discontinued
0.6525	Remote Similarity	NPD1930	Approved
0.6525	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6525	Remote Similarity	NPD1929	Approved
0.6512	Remote Similarity	NPD4136	Approved
0.6512	Remote Similarity	NPD3847	Discontinued
0.6512	Remote Similarity	NPD4135	Approved
0.6512	Remote Similarity	NPD4106	Approved
0.6512	Remote Similarity	NPD3496	Discontinued
0.6508	Remote Similarity	NPD4431	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD6048	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD6049	Phase 2
0.6491	Remote Similarity	NPD1693	Approved
0.6471	Remote Similarity	NPD3048	Approved
0.6471	Remote Similarity	NPD310	Approved
0.6471	Remote Similarity	NPD314	Approved
0.6471	Remote Similarity	NPD164	Approved
0.6471	Remote Similarity	NPD311	Approved
0.6471	Remote Similarity	NPD315	Approved
0.6471	Remote Similarity	NPD309	Approved
0.6471	Remote Similarity	NPD3047	Approved
0.6471	Remote Similarity	NPD3046	Approved
0.6471	Remote Similarity	NPD10	Approved
0.6466	Remote Similarity	NPD253	Approved
0.6466	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6466	Remote Similarity	NPD6085	Phase 2
0.646	Remote Similarity	NPD1088	Approved
0.6457	Remote Similarity	NPD1758	Phase 1
0.6455	Remote Similarity	NPD4793	Discontinued
0.6454	Remote Similarity	NPD5170	Discontinued
0.6446	Remote Similarity	NPD4095	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD9294	Approved
0.6441	Remote Similarity	NPD854	Approved
0.6441	Remote Similarity	NPD855	Approved
0.6435	Remote Similarity	NPD1989	Approved
0.6429	Remote Similarity	NPD1348	Approved
0.6429	Remote Similarity	NPD9256	Approved
0.6429	Remote Similarity	NPD9258	Approved
0.6423	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6423	Remote Similarity	NPD3643	Approved
0.6423	Remote Similarity	NPD3642	Approved
0.6423	Remote Similarity	NPD3644	Approved
0.6418	Remote Similarity	NPD3661	Approved
0.6418	Remote Similarity	NPD3664	Approved
0.6418	Remote Similarity	NPD3662	Phase 3
0.6418	Remote Similarity	NPD3663	Approved
0.6412	Remote Similarity	NPD2235	Phase 2
0.6412	Remote Similarity	NPD2231	Phase 2
0.641	Remote Similarity	NPD7798	Approved
0.6406	Remote Similarity	NPD1759	Phase 1
0.6406	Remote Similarity	NPD9545	Approved
0.6406	Remote Similarity	NPD4479	Discontinued
0.6406	Remote Similarity	NPD6093	Discontinued
0.6404	Remote Similarity	NPD719	Approved
0.6404	Remote Similarity	NPD720	Approved
0.6403	Remote Similarity	NPD2569	Approved
0.6403	Remote Similarity	NPD2567	Approved
0.6391	Remote Similarity	NPD2625	Approved
0.6391	Remote Similarity	NPD2628	Approved
0.6391	Remote Similarity	NPD2159	Approved
0.6391	Remote Similarity	NPD2627	Approved
0.6391	Remote Similarity	NPD2626	Approved
0.6391	Remote Similarity	NPD2797	Approved
0.6391	Remote Similarity	NPD2160	Approved
0.6389	Remote Similarity	NPD9491	Approved
0.6387	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD7978	Discontinued
0.6378	Remote Similarity	NPD3123	Discovery
0.6378	Remote Similarity	NPD9493	Approved
0.6377	Remote Similarity	NPD5124	Phase 1
0.6377	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6371	Remote Similarity	NPD9508	Approved
0.637	Remote Similarity	NPD2613	Approved
0.6364	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD3526	Approved
0.6364	Remote Similarity	NPD3524	Approved
0.6364	Remote Similarity	NPD5159	Phase 2
0.6364	Remote Similarity	NPD5157	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