NPASS Compound

Structure

NPC93027 OpenBabel07101718222D 27 30 0 0 1 0 0 0 0 0999 V2000 -4.8363 -2.9680 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 -2.1913 -2.4135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4980 -4.4543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 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 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1369 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 -0.1910 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 0.8660 -0.5000 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 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2109 -3.2953 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8581 -2.7601 0.0000 C 0 0 1 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 1.7321 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5491 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.1890 -3.5032 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.5417 -4.0385 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 4 25 1 0 0 0 0 5 27 1 0 0 0 0 6 7 1 0 0 0 0 6 17 2 0 0 0 0 8 9 1 0 0 0 0 8 20 2 0 0 0 0 9 21 1 0 0 0 0 10 12 1 0 0 0 0 10 18 1 0 0 0 0 11 13 1 0 0 0 0 11 22 1 0 0 0 0 12 23 1 0 0 0 0 13 24 1 0 0 0 0 14 17 1 0 0 0 0 14 18 1 0 0 0 0 15 25 1 0 0 0 0 15 26 2 0 0 0 0 16 1 1 1 0 0 0 16 20 1 0 0 0 0 16 25 1 0 0 0 0 17 23 1 0 0 0 0 18 27 1 1 0 0 0 19 7 1 6 0 0 0 19 21 1 0 0 0 0 19 22 1 0 0 0 0 20 24 1 0 0 0 0 21 24 1 1 0 0 0 22 23 1 1 0 0 0 23 2 1 1 0 0 0 24 3 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	371.28
Volume:	410.102
LogP:	4.721
LogD:	3.499
LogS:	-4.155
# Rotatable Bonds:	4
TPSA:	29.54
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.515
Synthetic Accessibility Score:	4.671
Fsp3:	0.792
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:	-4.518
MDCK Permeability:	8.859256013238337e-06
Pgp-inhibitor:	0.648
Pgp-substrate:	0.076
Human Intestinal Absorption (HIA):	0.013
20% Bioavailability (F20%):	0.489
30% Bioavailability (F30%):	0.026

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.383
Plasma Protein Binding (PPB):	72.21356964111328%
Volume Distribution (VD):	1.614
Pgp-substrate:	19.755834579467773%

ADMET: Metabolism

CYP1A2-inhibitor:	0.036
CYP1A2-substrate:	0.559
CYP2C19-inhibitor:	0.071
CYP2C19-substrate:	0.89
CYP2C9-inhibitor:	0.096
CYP2C9-substrate:	0.045
CYP2D6-inhibitor:	0.062
CYP2D6-substrate:	0.503
CYP3A4-inhibitor:	0.882
CYP3A4-substrate:	0.422

ADMET: Excretion

Clearance (CL):	6.807
Half-life (T1/2):	0.089

ADMET: Toxicity

hERG Blockers:	0.008
Human Hepatotoxicity (H-HT):	0.226
Drug-inuced Liver Injury (DILI):	0.048
AMES Toxicity:	0.018
Rat Oral Acute Toxicity:	0.946
Maximum Recommended Daily Dose:	0.927
Skin Sensitization:	0.351
Carcinogencity:	0.936
Eye Corrosion:	0.086
Eye Irritation:	0.072
Respiratory Toxicity:	0.986

Download Data

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

Natural Product: NPC93027

Natural Product ID:	NPC93027
*Common Name:**	N-[(S)-1-(3-Methoxy-10,13-Dimethyl-2,3,4,7,8,9,10,11,12,13,14,15-Dodecahydro-1H-Cyclopenta[A]Phenanthren-17-Yl)-Ethyl]-N-Methyl-Formamide
IUPAC Name:	N-[(1S)-1-[(3S,8R,9S,10R,13S,14S)-3-methoxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15-decahydro-1H-cyclopenta[a]phenanthren-17-yl]ethyl]-N-methylformamide
Synonyms:
Standard InCHIKey:	UWFDYAWULNEXBD-YULCGJSVSA-N
Standard InCHI:	InChI=1S/C24H37NO2/c1-16(25(4)15-26)20-8-9-21-19-7-6-17-14-18(27-5)10-12-23(17,2)22(19)11-13-24(20,21)3/h6,8,15-16,18-19,21-22H,7,9-14H2,1-5H3/t16-,18-,19-,21-,22-,23-,24+/m0/s1
SMILES:	C[C@@H](C1=CC[C@H]2[C@@H]3CC=C4C[C@H](CC[C@]4(C)[C@H]3CC[C@]12C)OC)N(C)C=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL140241
PubChem CID:	11773139
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0002340] Azasteroids and derivatives

*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
NPO27888	Sarcococca saligna	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14584959]
NPO27888	Sarcococca saligna	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14643329]
NPO27888	Sarcococca saligna	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9548847]
NPO27888	Sarcococca saligna	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27888	Sarcococca saligna	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27888	Sarcococca saligna	Species	Buxaceae	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
IC50	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT204	Individual Protein	Acetylcholinesterase	Homo sapiens	IC50	=	48977.88	nM	PMID[520878]

☑ 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 NPC93027 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	82
0.1-0.2	852
0.2-0.3	9401
0.3-0.4	17653
0.4-0.5	9484
0.5-0.6	4603
0.6-0.7	603
0.7-0.8	15
0.8-0.85	1
0.85-0.9	2
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8966	High Similarity	NPC75810
0.8681	High Similarity	NPC84171
0.8526	High Similarity	NPC140300
0.8	Intermediate Similarity	NPC247060
0.7822	Intermediate Similarity	NPC50815
0.7767	Intermediate Similarity	NPC86906
0.77	Intermediate Similarity	NPC91604
0.7677	Intermediate Similarity	NPC476903
0.7642	Intermediate Similarity	NPC63511
0.7609	Intermediate Similarity	NPC215474
0.76	Intermediate Similarity	NPC474164
0.75	Intermediate Similarity	NPC212874
0.7476	Intermediate Similarity	NPC176012
0.7474	Intermediate Similarity	NPC157479
0.7471	Intermediate Similarity	NPC265789
0.7431	Intermediate Similarity	NPC478137
0.7407	Intermediate Similarity	NPC79238
0.7358	Intermediate Similarity	NPC46981
0.7327	Intermediate Similarity	NPC289140
0.7308	Intermediate Similarity	NPC471083
0.73	Intermediate Similarity	NPC280710
0.73	Intermediate Similarity	NPC243985
0.7283	Intermediate Similarity	NPC44083
0.7283	Intermediate Similarity	NPC153987
0.7282	Intermediate Similarity	NPC135799
0.7264	Intermediate Similarity	NPC55462
0.7264	Intermediate Similarity	NPC195841
0.7264	Intermediate Similarity	NPC233256
0.7255	Intermediate Similarity	NPC240650
0.7238	Intermediate Similarity	NPC241879
0.7228	Intermediate Similarity	NPC272732
0.7228	Intermediate Similarity	NPC311164
0.7188	Intermediate Similarity	NPC147513
0.7182	Intermediate Similarity	NPC80834
0.7182	Intermediate Similarity	NPC469968
0.7156	Intermediate Similarity	NPC472313
0.7143	Intermediate Similarity	NPC321381
0.7143	Intermediate Similarity	NPC107059
0.7143	Intermediate Similarity	NPC321016
0.7079	Intermediate Similarity	NPC21773
0.7065	Intermediate Similarity	NPC198968
0.7065	Intermediate Similarity	NPC318495
0.7065	Intermediate Similarity	NPC155986
0.7064	Intermediate Similarity	NPC95920
0.7064	Intermediate Similarity	NPC147835
0.7064	Intermediate Similarity	NPC253645
0.7064	Intermediate Similarity	NPC85001
0.7048	Intermediate Similarity	NPC77703
0.7033	Intermediate Similarity	NPC288035
0.7033	Intermediate Similarity	NPC22105
0.7033	Intermediate Similarity	NPC136188
0.7033	Intermediate Similarity	NPC230301
0.7033	Intermediate Similarity	NPC162742
0.7033	Intermediate Similarity	NPC304309
0.7033	Intermediate Similarity	NPC134847
0.7033	Intermediate Similarity	NPC285893
0.7033	Intermediate Similarity	NPC28657
0.7027	Intermediate Similarity	NPC474452
0.7009	Intermediate Similarity	NPC119329
0.7009	Intermediate Similarity	NPC475239
0.7	Intermediate Similarity	NPC472359
0.6989	Remote Similarity	NPC474216
0.6989	Remote Similarity	NPC87604
0.6989	Remote Similarity	NPC475337
0.6989	Remote Similarity	NPC477522
0.6989	Remote Similarity	NPC473943
0.6972	Remote Similarity	NPC159367
0.6957	Remote Similarity	NPC240604
0.6957	Remote Similarity	NPC113733
0.6957	Remote Similarity	NPC300324
0.6952	Remote Similarity	NPC128698
0.6952	Remote Similarity	NPC239768
0.6952	Remote Similarity	NPC477964
0.6947	Remote Similarity	NPC474731
0.6947	Remote Similarity	NPC7505
0.6947	Remote Similarity	NPC474752
0.6947	Remote Similarity	NPC82986
0.6947	Remote Similarity	NPC474683
0.6947	Remote Similarity	NPC474759
0.6939	Remote Similarity	NPC166458
0.6937	Remote Similarity	NPC474459
0.6923	Remote Similarity	NPC476904
0.6916	Remote Similarity	NPC293299
0.6916	Remote Similarity	NPC45365
0.6915	Remote Similarity	NPC143182
0.6915	Remote Similarity	NPC81306
0.6915	Remote Similarity	NPC28862
0.6915	Remote Similarity	NPC328714
0.6915	Remote Similarity	NPC47982
0.6915	Remote Similarity	NPC84694
0.6915	Remote Similarity	NPC109546
0.6887	Remote Similarity	NPC118275
0.6882	Remote Similarity	NPC34019
0.6881	Remote Similarity	NPC25340
0.6875	Remote Similarity	NPC248886
0.6875	Remote Similarity	NPC5985
0.6848	Remote Similarity	NPC471723
0.6848	Remote Similarity	NPC141071
0.6848	Remote Similarity	NPC257347
0.6842	Remote Similarity	NPC26117
0.6842	Remote Similarity	NPC164840
0.6842	Remote Similarity	NPC241290
0.6842	Remote Similarity	NPC209944
0.6842	Remote Similarity	NPC234193
0.6822	Remote Similarity	NPC476755
0.6813	Remote Similarity	NPC471799
0.6809	Remote Similarity	NPC18603
0.6809	Remote Similarity	NPC307965
0.6809	Remote Similarity	NPC76931
0.6809	Remote Similarity	NPC275910
0.6804	Remote Similarity	NPC475789
0.68	Remote Similarity	NPC34754
0.6792	Remote Similarity	NPC275686
0.678	Remote Similarity	NPC472458
0.6774	Remote Similarity	NPC129165
0.6774	Remote Similarity	NPC7214
0.6774	Remote Similarity	NPC134330
0.6774	Remote Similarity	NPC189883
0.6774	Remote Similarity	NPC96319
0.6771	Remote Similarity	NPC23852
0.6771	Remote Similarity	NPC90150
0.6771	Remote Similarity	NPC470383
0.6771	Remote Similarity	NPC209620
0.6771	Remote Similarity	NPC47761
0.6771	Remote Similarity	NPC264245
0.6771	Remote Similarity	NPC474531
0.6771	Remote Similarity	NPC473534
0.6768	Remote Similarity	NPC264127
0.6768	Remote Similarity	NPC474970
0.6759	Remote Similarity	NPC474583
0.6759	Remote Similarity	NPC98765
0.6739	Remote Similarity	NPC471797
0.6737	Remote Similarity	NPC209430
0.6737	Remote Similarity	NPC472463
0.6737	Remote Similarity	NPC211322
0.6737	Remote Similarity	NPC1319
0.6737	Remote Similarity	NPC30986
0.6735	Remote Similarity	NPC472265
0.6735	Remote Similarity	NPC59453
0.6735	Remote Similarity	NPC33913
0.6735	Remote Similarity	NPC221758
0.6727	Remote Similarity	NPC169375
0.6726	Remote Similarity	NPC56796
0.6724	Remote Similarity	NPC474006
0.6702	Remote Similarity	NPC214570
0.6701	Remote Similarity	NPC1272
0.6701	Remote Similarity	NPC470049
0.6701	Remote Similarity	NPC189972
0.6701	Remote Similarity	NPC49964
0.6701	Remote Similarity	NPC470614
0.6701	Remote Similarity	NPC50964
0.6701	Remote Similarity	NPC101462
0.6696	Remote Similarity	NPC28280
0.6696	Remote Similarity	NPC304646
0.6695	Remote Similarity	NPC242692
0.6667	Remote Similarity	NPC236112
0.6667	Remote Similarity	NPC274448
0.6667	Remote Similarity	NPC266511
0.6667	Remote Similarity	NPC474189
0.6667	Remote Similarity	NPC476276
0.6667	Remote Similarity	NPC157257
0.6667	Remote Similarity	NPC474349
0.6639	Remote Similarity	NPC478138
0.6634	Remote Similarity	NPC97884
0.6634	Remote Similarity	NPC472220
0.6634	Remote Similarity	NPC470613
0.6634	Remote Similarity	NPC470612
0.6633	Remote Similarity	NPC470047
0.6633	Remote Similarity	NPC474634
0.6633	Remote Similarity	NPC470046
0.6633	Remote Similarity	NPC139206
0.6633	Remote Similarity	NPC317458
0.6632	Remote Similarity	NPC318136
0.6632	Remote Similarity	NPC285761
0.6632	Remote Similarity	NPC167037
0.6632	Remote Similarity	NPC6978
0.6632	Remote Similarity	NPC244385
0.6632	Remote Similarity	NPC312328
0.6632	Remote Similarity	NPC138621
0.6632	Remote Similarity	NPC477514
0.663	Remote Similarity	NPC474140
0.6606	Remote Similarity	NPC90538
0.6604	Remote Similarity	NPC4834
0.66	Remote Similarity	NPC155011
0.66	Remote Similarity	NPC145879
0.66	Remote Similarity	NPC51014
0.66	Remote Similarity	NPC474732
0.66	Remote Similarity	NPC474733
0.66	Remote Similarity	NPC474778
0.66	Remote Similarity	NPC31564
0.6598	Remote Similarity	NPC108476
0.6598	Remote Similarity	NPC109533
0.6596	Remote Similarity	NPC46160
0.6596	Remote Similarity	NPC73875
0.6596	Remote Similarity	NPC247325
0.6596	Remote Similarity	NPC237460
0.6596	Remote Similarity	NPC470362
0.6596	Remote Similarity	NPC244488
0.6596	Remote Similarity	NPC202642
0.6566	Remote Similarity	NPC474493

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 NPC93027 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	78
0.1-0.2	555
0.2-0.3	3229
0.3-0.4	3766
0.4-0.5	1190
0.5-0.6	304
0.6-0.7	27
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
0.7157	Intermediate Similarity	NPD5349	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD6942	Approved
0.7033	Intermediate Similarity	NPD7339	Approved
0.6789	Remote Similarity	NPD7333	Discontinued
0.6774	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD4786	Approved
0.6531	Remote Similarity	NPD3667	Approved
0.6495	Remote Similarity	NPD7525	Registered
0.64	Remote Similarity	NPD3668	Phase 3
0.6392	Remote Similarity	NPD7645	Phase 2
0.6383	Remote Similarity	NPD6926	Approved
0.6383	Remote Similarity	NPD6924	Approved
0.6383	Remote Similarity	NPD4784	Approved
0.6383	Remote Similarity	NPD4785	Approved
0.6381	Remote Similarity	NPD6399	Phase 3
0.6344	Remote Similarity	NPD4243	Approved
0.6293	Remote Similarity	NPD7336	Phase 2
0.6293	Remote Similarity	NPD7335	Phase 2
0.6293	Remote Similarity	NPD7337	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD7146	Approved
0.6275	Remote Similarity	NPD6409	Approved
0.6275	Remote Similarity	NPD5330	Approved
0.6275	Remote Similarity	NPD7521	Approved
0.6275	Remote Similarity	NPD6684	Approved
0.6275	Remote Similarity	NPD7334	Approved
0.625	Remote Similarity	NPD6051	Approved
0.625	Remote Similarity	NPD5328	Approved
0.625	Remote Similarity	NPD6933	Approved
0.6214	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.617	Remote Similarity	NPD7152	Approved
0.617	Remote Similarity	NPD7151	Approved
0.617	Remote Similarity	NPD7150	Approved
0.6168	Remote Similarity	NPD5771	Approved
0.6162	Remote Similarity	NPD7509	Discontinued
0.6154	Remote Similarity	NPD6903	Approved
0.6154	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD5737	Approved
0.6154	Remote Similarity	NPD6672	Approved
0.6132	Remote Similarity	NPD6079	Approved
0.6129	Remote Similarity	NPD6923	Approved
0.6129	Remote Similarity	NPD6922	Approved
0.6117	Remote Similarity	NPD3618	Phase 1
0.6078	Remote Similarity	NPD3133	Approved
0.6078	Remote Similarity	NPD3665	Phase 1
0.6078	Remote Similarity	NPD3666	Approved
0.6064	Remote Similarity	NPD7144	Approved
0.6064	Remote Similarity	NPD7143	Approved
0.6061	Remote Similarity	NPD4195	Approved
0.6061	Remote Similarity	NPD6929	Approved
0.6048	Remote Similarity	NPD7122	Discontinued
0.6019	Remote Similarity	NPD5707	Approved
0.6017	Remote Similarity	NPD8077	Approved
0.6017	Remote Similarity	NPD8078	Approved
0.6016	Remote Similarity	NPD6909	Approved
0.6016	Remote Similarity	NPD6908	Approved
0.6	Remote Similarity	NPD4748	Discontinued
0.6	Remote Similarity	NPD4723	Approved
0.6	Remote Similarity	NPD6930	Phase 2
0.6	Remote Similarity	NPD4722	Approved
0.6	Remote Similarity	NPD6931	Approved
0.598	Remote Similarity	NPD6695	Phase 3
0.5979	Remote Similarity	NPD4190	Phase 3
0.5979	Remote Similarity	NPD5275	Approved
0.5962	Remote Similarity	NPD8308	Discontinued
0.5962	Remote Similarity	NPD6098	Approved
0.596	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD4202	Approved
0.5923	Remote Similarity	NPD8449	Approved
0.5922	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD4697	Phase 3
0.5882	Remote Similarity	NPD4221	Approved
0.5882	Remote Similarity	NPD4223	Phase 3
0.5878	Remote Similarity	NPD8450	Suspended
0.5868	Remote Similarity	NPD7755	Approved
0.5868	Remote Similarity	NPD7754	Approved
0.5865	Remote Similarity	NPD5329	Approved
0.5862	Remote Similarity	NPD5706	Approved
0.5862	Remote Similarity	NPD5705	Approved
0.5862	Remote Similarity	NPD5704	Approved
0.5859	Remote Similarity	NPD6925	Approved
0.5859	Remote Similarity	NPD5776	Phase 2
0.5859	Remote Similarity	NPD6932	Approved
0.5842	Remote Similarity	NPD7332	Phase 2
0.581	Remote Similarity	NPD5279	Phase 3
0.58	Remote Similarity	NPD7145	Approved
0.5794	Remote Similarity	NPD6080	Approved
0.5794	Remote Similarity	NPD6673	Approved
0.5794	Remote Similarity	NPD4753	Phase 2
0.5794	Remote Similarity	NPD6904	Approved
0.5784	Remote Similarity	NPD6898	Phase 1
0.5776	Remote Similarity	NPD6640	Phase 3
0.5769	Remote Similarity	NPD4197	Approved
0.5766	Remote Similarity	NPD5221	Approved
0.5766	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5766	Remote Similarity	NPD5222	Approved
0.5758	Remote Similarity	NPD1346	Approved
0.5755	Remote Similarity	NPD7524	Approved
0.5755	Remote Similarity	NPD7750	Discontinued
0.5743	Remote Similarity	NPD6683	Phase 2
0.5736	Remote Similarity	NPD8337	Approved
0.5736	Remote Similarity	NPD8336	Approved
0.5729	Remote Similarity	NPD6938	Clinical (unspecified phase)
0.5729	Remote Similarity	NPD6939	Phase 2
0.5729	Remote Similarity	NPD4747	Approved
0.5727	Remote Similarity	NPD5769	Clinical (unspecified phase)
0.5727	Remote Similarity	NPD7900	Approved
0.5727	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5727	Remote Similarity	NPD7748	Approved
0.5714	Remote Similarity	NPD6083	Phase 2
0.5714	Remote Similarity	NPD6893	Approved
0.5714	Remote Similarity	NPD6084	Phase 2
0.5714	Remote Similarity	NPD5173	Approved
0.5714	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD4755	Approved
0.5701	Remote Similarity	NPD5208	Approved
0.5688	Remote Similarity	NPD7515	Phase 2
0.5686	Remote Similarity	NPD7514	Phase 3
0.5676	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5664	Remote Similarity	NPD7638	Approved
0.566	Remote Similarity	NPD4689	Approved
0.566	Remote Similarity	NPD5205	Approved
0.566	Remote Similarity	NPD4688	Approved
0.566	Remote Similarity	NPD4138	Approved
0.566	Remote Similarity	NPD4693	Phase 3
0.566	Remote Similarity	NPD4690	Approved
0.5657	Remote Similarity	NPD8264	Approved
0.5652	Remote Similarity	NPD4719	Phase 2
0.5641	Remote Similarity	NPD6008	Approved
0.5641	Remote Similarity	NPD6675	Approved
0.5641	Remote Similarity	NPD5739	Approved
0.5641	Remote Similarity	NPD6920	Discontinued
0.5641	Remote Similarity	NPD6402	Approved
0.5641	Remote Similarity	NPD7128	Approved
0.5631	Remote Similarity	NPD6902	Approved
0.5625	Remote Similarity	NPD4137	Phase 3
0.5614	Remote Similarity	NPD6404	Discontinued
0.5614	Remote Similarity	NPD4700	Approved
0.5614	Remote Similarity	NPD7640	Approved
0.5614	Remote Similarity	NPD4696	Approved
0.5614	Remote Similarity	NPD5285	Approved
0.5614	Remote Similarity	NPD7639	Approved
0.5614	Remote Similarity	NPD5286	Approved
0.5603	Remote Similarity	NPD7987	Approved
0.5603	Remote Similarity	NPD7911	Approved
0.5603	Remote Similarity	NPD7912	Approved
0.5603	Remote Similarity	NPD7986	Approved
0.56	Remote Similarity	NPD7519	Approved
0.56	Remote Similarity	NPD7517	Approved
0.56	Remote Similarity	NPD7518	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