NPASS Compound

Structure

NPC140300 OpenBabel07101718182D 27 30 0 0 1 0 0 0 0 0999 V2000 -6.5683 -3.9680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9234 -3.4135 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 -5.2301 -5.4543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9429 -4.2953 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 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8690 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2812 -1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 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 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5902 -3.7601 0.0000 C 0 0 1 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 -3.4641 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.2812 -2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 C 0 0 1 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 -0.0000 -1.0000 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 -4.3301 -2.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.9211 -4.5032 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4 25 1 0 0 0 0 5 25 1 0 0 0 0 6 27 1 0 0 0 0 7 8 1 0 0 0 0 7 16 2 0 0 0 0 9 10 1 0 0 0 0 9 18 2 0 0 0 0 10 19 1 0 0 0 0 11 12 1 0 0 0 0 11 20 1 0 0 0 0 12 23 1 0 0 0 0 13 16 1 0 0 0 0 13 22 1 0 0 0 0 14 21 1 0 0 0 0 14 24 1 0 0 0 0 15 1 1 1 0 0 0 15 18 1 0 0 0 0 15 25 1 0 0 0 0 16 24 1 0 0 0 0 17 8 1 6 0 0 0 17 19 1 0 0 0 0 17 20 1 0 0 0 0 18 23 1 0 0 0 0 19 23 1 1 0 0 0 20 24 1 1 0 0 0 21 22 1 0 0 0 0 21 26 1 1 0 0 0 22 27 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:	373.3
Volume:	412.739
LogP:	4.38
LogD:	3.661
LogS:	-3.597
# Rotatable Bonds:	3
TPSA:	32.7
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.743
Synthetic Accessibility Score:	4.766
Fsp3:	0.833
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:	-4.671
MDCK Permeability:	1.1124277079943568e-05
Pgp-inhibitor:	0.996
Pgp-substrate:	0.633
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.62
30% Bioavailability (F30%):	0.007

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.8
Plasma Protein Binding (PPB):	73.26786041259766%
Volume Distribution (VD):	2.516
Pgp-substrate:	31.47495460510254%

ADMET: Metabolism

CYP1A2-inhibitor:	0.031
CYP1A2-substrate:	0.209
CYP2C19-inhibitor:	0.024
CYP2C19-substrate:	0.946
CYP2C9-inhibitor:	0.049
CYP2C9-substrate:	0.052
CYP2D6-inhibitor:	0.719
CYP2D6-substrate:	0.862
CYP3A4-inhibitor:	0.867
CYP3A4-substrate:	0.681

ADMET: Excretion

Clearance (CL):	13.521
Half-life (T1/2):	0.124

ADMET: Toxicity

hERG Blockers:	0.043
Human Hepatotoxicity (H-HT):	0.248
Drug-inuced Liver Injury (DILI):	0.088
AMES Toxicity:	0.015
Rat Oral Acute Toxicity:	0.945
Maximum Recommended Daily Dose:	0.907
Skin Sensitization:	0.193
Carcinogencity:	0.914
Eye Corrosion:	0.023
Eye Irritation:	0.024
Respiratory Toxicity:	0.988

Download Data

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

Natural Product: NPC140300

Natural Product ID:	NPC140300
*Common Name:**	(2S,3R,8R,9S,10R,13S,14S)-17-[(1S)-1-(Dimethylamino)Ethyl]-3-Methoxy-10,13-Dimethyl-2,3,4,7,8,9,11,12,14,15-Decahydro-1H-Cyclopenta[A]Phenanthren-2-Ol
IUPAC Name:	(2S,3R,8R,9S,10R,13S,14S)-17-[(1S)-1-(dimethylamino)ethyl]-3-methoxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15-decahydro-1H-cyclopenta[a]phenanthren-2-ol
Synonyms:
Standard InCHIKey:	NGSWUPZJKYFTDE-FADSCHIBSA-N
Standard InCHI:	InChI=1S/C24H39NO2/c1-15(25(4)5)18-9-10-19-17-8-7-16-13-22(27-6)21(26)14-24(16,3)20(17)11-12-23(18,19)2/h7,9,15,17,19-22,26H,8,10-14H2,1-6H3/t15-,17-,19-,20-,21-,22+,23+,24-/m0/s1
SMILES:	C[C@@H](C1=CC[C@H]2[C@@H]3CC=C4C[C@H]([C@H](C[C@]4(C)[C@H]3CC[C@]12C)O)OC)N(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL136686
PubChem CID:	11314804
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001295] Hydroxysteroids

*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	=	251188.64	nM	PMID[506965]

☑ 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 NPC140300 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	706
0.2-0.3	5141
0.3-0.4	18612
0.4-0.5	9749
0.5-0.6	6646
0.6-0.7	1607
0.7-0.8	149
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8571	High Similarity	NPC75810
0.8526	High Similarity	NPC93027
0.84	Intermediate Similarity	NPC247060
0.8316	Intermediate Similarity	NPC84171
0.8265	Intermediate Similarity	NPC476903
0.8218	Intermediate Similarity	NPC50815
0.81	Intermediate Similarity	NPC91604
0.8	Intermediate Similarity	NPC474164
0.7961	Intermediate Similarity	NPC45365
0.7961	Intermediate Similarity	NPC293299
0.7935	Intermediate Similarity	NPC474531
0.7905	Intermediate Similarity	NPC46981
0.79	Intermediate Similarity	NPC289140
0.7885	Intermediate Similarity	NPC212874
0.7864	Intermediate Similarity	NPC471083
0.7864	Intermediate Similarity	NPC176012
0.7826	Intermediate Similarity	NPC236112
0.781	Intermediate Similarity	NPC55462
0.7788	Intermediate Similarity	NPC241879
0.7766	Intermediate Similarity	NPC317458
0.7742	Intermediate Similarity	NPC109533
0.7719	Intermediate Similarity	NPC478138
0.7717	Intermediate Similarity	NPC328714
0.77	Intermediate Similarity	NPC280710
0.77	Intermediate Similarity	NPC243985
0.767	Intermediate Similarity	NPC135799
0.7647	Intermediate Similarity	NPC240650
0.7636	Intermediate Similarity	NPC478137
0.7624	Intermediate Similarity	NPC311164
0.7624	Intermediate Similarity	NPC272732
0.7582	Intermediate Similarity	NPC321016
0.7582	Intermediate Similarity	NPC321381
0.7582	Intermediate Similarity	NPC107059
0.7526	Intermediate Similarity	NPC477604
0.7526	Intermediate Similarity	NPC94462
0.7526	Intermediate Similarity	NPC125399
0.7523	Intermediate Similarity	NPC472359
0.75	Intermediate Similarity	NPC198968
0.75	Intermediate Similarity	NPC318495
0.75	Intermediate Similarity	NPC159367
0.75	Intermediate Similarity	NPC155986
0.7477	Intermediate Similarity	NPC86906
0.7474	Intermediate Similarity	NPC248886
0.7474	Intermediate Similarity	NPC30166
0.7473	Intermediate Similarity	NPC28657
0.7473	Intermediate Similarity	NPC257347
0.7473	Intermediate Similarity	NPC162742
0.7473	Intermediate Similarity	NPC230301
0.7473	Intermediate Similarity	NPC477923
0.7473	Intermediate Similarity	NPC22105
0.7473	Intermediate Similarity	NPC66566
0.7473	Intermediate Similarity	NPC141071
0.7473	Intermediate Similarity	NPC288035
0.7473	Intermediate Similarity	NPC471723
0.7473	Intermediate Similarity	NPC134847
0.7473	Intermediate Similarity	NPC285893
0.7473	Intermediate Similarity	NPC304309
0.7473	Intermediate Similarity	NPC136188
0.7447	Intermediate Similarity	NPC13554
0.7431	Intermediate Similarity	NPC147835
0.7431	Intermediate Similarity	NPC85001
0.7431	Intermediate Similarity	NPC95920
0.7431	Intermediate Similarity	NPC253645
0.7419	Intermediate Similarity	NPC477522
0.7419	Intermediate Similarity	NPC473943
0.7419	Intermediate Similarity	NPC474216
0.7419	Intermediate Similarity	NPC87604
0.7419	Intermediate Similarity	NPC275910
0.7407	Intermediate Similarity	NPC25340
0.7396	Intermediate Similarity	NPC207013
0.7396	Intermediate Similarity	NPC474634
0.7391	Intermediate Similarity	NPC113733
0.7391	Intermediate Similarity	NPC477925
0.7391	Intermediate Similarity	NPC129165
0.7391	Intermediate Similarity	NPC240604
0.7391	Intermediate Similarity	NPC274079
0.7391	Intermediate Similarity	NPC300324
0.7391	Intermediate Similarity	NPC189883
0.7391	Intermediate Similarity	NPC134330
0.7383	Intermediate Similarity	NPC475239
0.7374	Intermediate Similarity	NPC474668
0.7368	Intermediate Similarity	NPC474759
0.7368	Intermediate Similarity	NPC474752
0.7368	Intermediate Similarity	NPC82986
0.7368	Intermediate Similarity	NPC7505
0.7368	Intermediate Similarity	NPC474731
0.7368	Intermediate Similarity	NPC70927
0.7368	Intermediate Similarity	NPC474683
0.734	Intermediate Similarity	NPC47982
0.734	Intermediate Similarity	NPC109546
0.734	Intermediate Similarity	NPC28862
0.734	Intermediate Similarity	NPC84694
0.734	Intermediate Similarity	NPC1319
0.734	Intermediate Similarity	NPC209430
0.734	Intermediate Similarity	NPC81306
0.734	Intermediate Similarity	NPC143182
0.734	Intermediate Similarity	NPC30986
0.734	Intermediate Similarity	NPC472463
0.732	Intermediate Similarity	NPC185568
0.7312	Intermediate Similarity	NPC477924
0.7312	Intermediate Similarity	NPC34019
0.7312	Intermediate Similarity	NPC214570
0.73	Intermediate Similarity	NPC477606
0.73	Intermediate Similarity	NPC105495
0.7292	Intermediate Similarity	NPC470049
0.7292	Intermediate Similarity	NPC5985
0.729	Intermediate Similarity	NPC474583
0.7264	Intermediate Similarity	NPC118275
0.7263	Intermediate Similarity	NPC22403
0.7263	Intermediate Similarity	NPC209944
0.7263	Intermediate Similarity	NPC164840
0.7263	Intermediate Similarity	NPC26117
0.7263	Intermediate Similarity	NPC241290
0.7263	Intermediate Similarity	NPC287749
0.7263	Intermediate Similarity	NPC234193
0.7253	Intermediate Similarity	NPC471799
0.7234	Intermediate Similarity	NPC6978
0.7234	Intermediate Similarity	NPC285761
0.7234	Intermediate Similarity	NPC18603
0.7234	Intermediate Similarity	NPC307965
0.7234	Intermediate Similarity	NPC83351
0.7234	Intermediate Similarity	NPC244385
0.7234	Intermediate Similarity	NPC167891
0.7234	Intermediate Similarity	NPC312328
0.7234	Intermediate Similarity	NPC318136
0.7234	Intermediate Similarity	NPC76931
0.7234	Intermediate Similarity	NPC138621
0.7234	Intermediate Similarity	NPC167037
0.7232	Intermediate Similarity	NPC56796
0.7232	Intermediate Similarity	NPC80834
0.7232	Intermediate Similarity	NPC469968
0.7227	Intermediate Similarity	NPC48886
0.7227	Intermediate Similarity	NPC265275
0.7227	Intermediate Similarity	NPC94881
0.7216	Intermediate Similarity	NPC475789
0.7204	Intermediate Similarity	NPC73875
0.7204	Intermediate Similarity	NPC96319
0.7204	Intermediate Similarity	NPC470362
0.7204	Intermediate Similarity	NPC46160
0.7204	Intermediate Similarity	NPC202642
0.7204	Intermediate Similarity	NPC237460
0.72	Intermediate Similarity	NPC133588
0.72	Intermediate Similarity	NPC34754
0.7188	Intermediate Similarity	NPC6707
0.7188	Intermediate Similarity	NPC470383
0.7188	Intermediate Similarity	NPC47761
0.7188	Intermediate Similarity	NPC23852
0.7188	Intermediate Similarity	NPC209620
0.7188	Intermediate Similarity	NPC264245
0.7184	Intermediate Similarity	NPC65402
0.7184	Intermediate Similarity	NPC127718
0.7174	Intermediate Similarity	NPC477138
0.7174	Intermediate Similarity	NPC471797
0.7174	Intermediate Similarity	NPC243342
0.7172	Intermediate Similarity	NPC71520
0.7172	Intermediate Similarity	NPC474970
0.7172	Intermediate Similarity	NPC269058
0.7172	Intermediate Similarity	NPC166458
0.717	Intermediate Similarity	NPC275686
0.7158	Intermediate Similarity	NPC80530
0.7158	Intermediate Similarity	NPC273410
0.7157	Intermediate Similarity	NPC210268
0.7143	Intermediate Similarity	NPC242001
0.7143	Intermediate Similarity	NPC79238
0.7143	Intermediate Similarity	NPC474493
0.7143	Intermediate Similarity	NPC319238
0.7143	Intermediate Similarity	NPC470077
0.7143	Intermediate Similarity	NPC474047
0.7143	Intermediate Similarity	NPC475033
0.7143	Intermediate Similarity	NPC296686
0.7143	Intermediate Similarity	NPC209802
0.7143	Intermediate Similarity	NPC265789
0.7143	Intermediate Similarity	NPC124172
0.7143	Intermediate Similarity	NPC475032
0.7143	Intermediate Similarity	NPC238992
0.7129	Intermediate Similarity	NPC470361
0.7128	Intermediate Similarity	NPC471798
0.7128	Intermediate Similarity	NPC130136
0.7115	Intermediate Similarity	NPC8774
0.7113	Intermediate Similarity	NPC470614
0.7113	Intermediate Similarity	NPC101462
0.7113	Intermediate Similarity	NPC189972
0.7113	Intermediate Similarity	NPC1272
0.7113	Intermediate Similarity	NPC47763
0.7113	Intermediate Similarity	NPC49964
0.7113	Intermediate Similarity	NPC7988
0.7113	Intermediate Similarity	NPC50964
0.7113	Intermediate Similarity	NPC201852
0.71	Intermediate Similarity	NPC470620
0.7097	Intermediate Similarity	NPC291503
0.7097	Intermediate Similarity	NPC118508
0.7097	Intermediate Similarity	NPC322353
0.7097	Intermediate Similarity	NPC121744
0.7091	Intermediate Similarity	NPC169375
0.7087	Intermediate Similarity	NPC307776
0.7087	Intermediate Similarity	NPC98193
0.7083	Intermediate Similarity	NPC236237
0.7083	Intermediate Similarity	NPC102253
0.7083	Intermediate Similarity	NPC322313
0.7071	Intermediate Similarity	NPC474189

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 NPC140300 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	85
0.1-0.2	481
0.2-0.3	3183
0.3-0.4	3671
0.4-0.5	1270
0.5-0.6	406
0.6-0.7	51
0.7-0.8	3
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
0.7473	Intermediate Similarity	NPD7339	Approved
0.7473	Intermediate Similarity	NPD6942	Approved
0.7204	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD7525	Registered
0.7021	Intermediate Similarity	NPD6933	Approved
0.6979	Remote Similarity	NPD7645	Phase 2
0.697	Remote Similarity	NPD4786	Approved
0.6809	Remote Similarity	NPD6924	Approved
0.6809	Remote Similarity	NPD6926	Approved
0.6768	Remote Similarity	NPD3667	Approved
0.6765	Remote Similarity	NPD7524	Approved
0.6735	Remote Similarity	NPD7509	Discontinued
0.6729	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD4159	Approved
0.6635	Remote Similarity	NPD5328	Approved
0.6632	Remote Similarity	NPD4784	Approved
0.6632	Remote Similarity	NPD4785	Approved
0.6614	Remote Similarity	NPD8449	Approved
0.6602	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD4243	Approved
0.6596	Remote Similarity	NPD7150	Approved
0.6596	Remote Similarity	NPD7151	Approved
0.6596	Remote Similarity	NPD7152	Approved
0.6566	Remote Similarity	NPD4748	Discontinued
0.6562	Remote Similarity	NPD8450	Suspended
0.6559	Remote Similarity	NPD6923	Approved
0.6559	Remote Similarity	NPD6922	Approved
0.6549	Remote Similarity	NPD7333	Discontinued
0.6549	Remote Similarity	NPD6640	Phase 3
0.6509	Remote Similarity	NPD6079	Approved
0.6505	Remote Similarity	NPD3618	Phase 1
0.6489	Remote Similarity	NPD7144	Approved
0.6489	Remote Similarity	NPD7143	Approved
0.6465	Remote Similarity	NPD6929	Approved
0.6449	Remote Similarity	NPD6399	Phase 3
0.64	Remote Similarity	NPD6930	Phase 2
0.64	Remote Similarity	NPD6931	Approved
0.6389	Remote Similarity	NPD5771	Approved
0.6373	Remote Similarity	NPD6695	Phase 3
0.6364	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6341	Remote Similarity	NPD6909	Approved
0.6341	Remote Similarity	NPD6908	Approved
0.6311	Remote Similarity	NPD3666	Approved
0.6311	Remote Similarity	NPD3665	Phase 1
0.6311	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD3133	Approved
0.6296	Remote Similarity	NPD4202	Approved
0.6263	Remote Similarity	NPD5776	Phase 2
0.6263	Remote Similarity	NPD6932	Approved
0.6263	Remote Similarity	NPD6925	Approved
0.6238	Remote Similarity	NPD7332	Phase 2
0.6226	Remote Similarity	NPD4723	Approved
0.6226	Remote Similarity	NPD4722	Approved
0.6224	Remote Similarity	NPD5275	Approved
0.6224	Remote Similarity	NPD4190	Phase 3
0.6224	Remote Similarity	NPD8264	Approved
0.62	Remote Similarity	NPD7145	Approved
0.6198	Remote Similarity	NPD7754	Approved
0.6198	Remote Similarity	NPD7755	Approved
0.6176	Remote Similarity	NPD6898	Phase 1
0.6154	Remote Similarity	NPD3668	Phase 3
0.6139	Remote Similarity	NPD6683	Phase 2
0.6139	Remote Similarity	NPD4195	Approved
0.6132	Remote Similarity	NPD7750	Discontinued
0.6126	Remote Similarity	NPD4697	Phase 3
0.6126	Remote Similarity	NPD5221	Approved
0.6126	Remote Similarity	NPD5222	Approved
0.6126	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6095	Remote Similarity	NPD6893	Approved
0.6095	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6083	Remote Similarity	NPD7335	Phase 2
0.6083	Remote Similarity	NPD7336	Phase 2
0.6083	Remote Similarity	NPD7337	Clinical (unspecified phase)
0.6078	Remote Similarity	NPD7514	Phase 3
0.6071	Remote Similarity	NPD7919	Phase 3
0.6071	Remote Similarity	NPD4755	Approved
0.6071	Remote Similarity	NPD7920	Phase 3
0.6071	Remote Similarity	NPD5173	Approved
0.6055	Remote Similarity	NPD7515	Phase 2
0.6042	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6038	Remote Similarity	NPD5279	Phase 3
0.6019	Remote Similarity	NPD6902	Approved
0.6019	Remote Similarity	NPD4753	Phase 2
0.6018	Remote Similarity	NPD7638	Approved
0.6018	Remote Similarity	NPD8088	Phase 1
0.6018	Remote Similarity	NPD4225	Approved
0.6016	Remote Similarity	NPD7115	Discovery
0.6	Remote Similarity	NPD4719	Phase 2
0.5984	Remote Similarity	NPD7122	Discontinued
0.5983	Remote Similarity	NPD6920	Discontinued
0.5983	Remote Similarity	NPD6675	Approved
0.5983	Remote Similarity	NPD5357	Phase 1
0.5983	Remote Similarity	NPD5739	Approved
0.5983	Remote Similarity	NPD6402	Approved
0.5983	Remote Similarity	NPD7128	Approved
0.5965	Remote Similarity	NPD4700	Approved
0.5965	Remote Similarity	NPD5285	Approved
0.5965	Remote Similarity	NPD5286	Approved
0.5965	Remote Similarity	NPD4696	Approved
0.5965	Remote Similarity	NPD7639	Approved
0.5965	Remote Similarity	NPD7640	Approved
0.5962	Remote Similarity	NPD4223	Phase 3
0.5962	Remote Similarity	NPD4221	Approved
0.595	Remote Similarity	NPD8297	Approved
0.5946	Remote Similarity	NPD7748	Approved
0.5943	Remote Similarity	NPD5329	Approved
0.5932	Remote Similarity	NPD6412	Phase 2
0.5929	Remote Similarity	NPD6084	Phase 2
0.5929	Remote Similarity	NPD6083	Phase 2
0.5913	Remote Similarity	NPD5223	Approved
0.5909	Remote Similarity	NPD7087	Discontinued
0.5902	Remote Similarity	NPD4632	Approved
0.5888	Remote Similarity	NPD7521	Approved
0.5888	Remote Similarity	NPD6409	Approved
0.5888	Remote Similarity	NPD8308	Discontinued
0.5888	Remote Similarity	NPD7334	Approved
0.5888	Remote Similarity	NPD5330	Approved
0.5888	Remote Similarity	NPD7146	Approved
0.5888	Remote Similarity	NPD6684	Approved
0.5882	Remote Similarity	NPD6881	Approved
0.5882	Remote Similarity	NPD7320	Approved
0.5882	Remote Similarity	NPD6415	Discontinued
0.5882	Remote Similarity	NPD6899	Approved
0.5877	Remote Similarity	NPD5290	Discontinued
0.5872	Remote Similarity	NPD6051	Approved
0.5862	Remote Similarity	NPD5224	Approved
0.5862	Remote Similarity	NPD4633	Approved
0.5862	Remote Similarity	NPD5211	Phase 2
0.5862	Remote Similarity	NPD5225	Approved
0.5862	Remote Similarity	NPD5226	Approved
0.5859	Remote Similarity	NPD7604	Phase 2
0.5849	Remote Similarity	NPD4197	Approved
0.5833	Remote Similarity	NPD6372	Approved
0.5833	Remote Similarity	NPD6373	Approved
0.5827	Remote Similarity	NPD6921	Approved
0.582	Remote Similarity	NPD8078	Approved
0.582	Remote Similarity	NPD8077	Approved
0.5818	Remote Similarity	NPD3168	Discontinued
0.5812	Remote Similarity	NPD5174	Approved
0.5812	Remote Similarity	NPD4754	Approved
0.5812	Remote Similarity	NPD5175	Approved
0.5804	Remote Similarity	NPD5707	Approved
0.5798	Remote Similarity	NPD5701	Approved
0.5798	Remote Similarity	NPD7646	Clinical (unspecified phase)
0.5798	Remote Similarity	NPD5697	Approved
0.5794	Remote Similarity	NPD7517	Approved
0.5794	Remote Similarity	NPD7516	Approved
0.5794	Remote Similarity	NPD7522	Discontinued
0.5794	Remote Similarity	NPD7518	Approved
0.5794	Remote Similarity	NPD7519	Approved
0.5789	Remote Similarity	NPD7902	Approved
0.5785	Remote Similarity	NPD6883	Approved
0.5785	Remote Similarity	NPD7290	Approved
0.5785	Remote Similarity	NPD4634	Approved
0.5785	Remote Similarity	NPD7102	Approved
0.578	Remote Similarity	NPD6903	Approved
0.578	Remote Similarity	NPD6672	Approved
0.578	Remote Similarity	NPD5737	Approved
0.578	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5766	Remote Similarity	NPD8034	Phase 2
0.5766	Remote Similarity	NPD8035	Phase 2
0.5763	Remote Similarity	NPD5141	Approved
0.5755	Remote Similarity	NPD4788	Approved
0.5752	Remote Similarity	NPD7991	Discontinued
0.5752	Remote Similarity	NPD5210	Approved
0.5752	Remote Similarity	NPD4629	Approved
0.575	Remote Similarity	NPD6011	Approved
0.5741	Remote Similarity	NPD4689	Approved
0.5741	Remote Similarity	NPD4138	Approved
0.5741	Remote Similarity	NPD4693	Phase 3
0.5741	Remote Similarity	NPD5205	Approved
0.5741	Remote Similarity	NPD4690	Approved
0.5741	Remote Similarity	NPD4688	Approved
0.5738	Remote Similarity	NPD6847	Approved
0.5738	Remote Similarity	NPD6650	Approved
0.5738	Remote Similarity	NPD6617	Approved
0.5738	Remote Similarity	NPD6649	Approved
0.5738	Remote Similarity	NPD8130	Phase 1
0.5738	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5738	Remote Similarity	NPD6869	Approved
0.5714	Remote Similarity	NPD7328	Approved
0.5714	Remote Similarity	NPD4767	Approved
0.5714	Remote Similarity	NPD4768	Approved
0.5714	Remote Similarity	NPD7327	Approved
0.5703	Remote Similarity	NPD8033	Approved
0.5702	Remote Similarity	NPD6013	Approved
0.5702	Remote Similarity	NPD6014	Approved
0.5702	Remote Similarity	NPD6012	Approved
0.5691	Remote Similarity	NPD6882	Approved
0.569	Remote Similarity	NPD6404	Discontinued
0.569	Remote Similarity	NPD8418	Phase 2
0.5686	Remote Similarity	NPD1346	Approved
0.5682	Remote Similarity	NPD8337	Approved
0.5682	Remote Similarity	NPD8336	Approved
0.5676	Remote Similarity	NPD4001	Clinical (unspecified phase)
0.5676	Remote Similarity	NPD7136	Phase 2
0.5676	Remote Similarity	NPD4096	Approved
0.5672	Remote Similarity	NPD7260	Phase 2
0.5664	Remote Similarity	NPD5769	Clinical (unspecified phase)
0.5659	Remote Similarity	NPD7725	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