NPASS Compound

Structure

NPC51499 OpenBabel07101719122D 32 36 0 0 1 0 0 0 0 0999 V2000 3.5491 2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1472 -1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6472 -0.8250 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -2.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -0.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 -3.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1472 -2.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 -2.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 3.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 1.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.2812 -1.1910 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5491 -1.1910 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.6831 0.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.8171 -1.1910 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 0.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.1472 -1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 -1.6910 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.5491 -0.1910 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.8171 -0.1910 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6831 4.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -1.6910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5878 0.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 2.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 15 1 0 0 0 0 2 24 1 0 0 0 0 3 24 1 0 0 0 0 7 9 1 0 0 0 0 7 10 1 0 0 0 0 8 11 1 0 0 0 0 8 18 1 0 0 0 0 9 24 1 0 0 0 0 10 25 1 0 0 0 0 11 26 1 0 0 0 0 12 16 2 0 0 0 0 12 22 1 0 0 0 0 13 17 1 0 0 0 0 13 20 1 0 0 0 0 14 19 1 0 0 0 0 14 21 1 0 0 0 0 15 28 2 0 0 0 0 15 31 1 0 0 0 0 16 17 1 0 0 0 0 16 23 1 0 0 0 0 17 31 1 1 0 0 0 18 24 1 0 0 0 0 18 25 1 1 0 0 0 19 25 1 1 0 0 0 19 26 1 0 0 0 0 20 26 1 1 0 0 0 20 27 1 0 0 0 0 21 27 1 1 0 0 0 21 29 1 0 0 0 0 22 30 2 0 0 0 0 22 32 1 0 0 0 0 23 27 1 1 0 0 0 23 32 1 0 0 0 0 25 4 1 1 0 0 0 26 5 1 1 0 0 0 27 6 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	250.12
Volume:	252.282
LogP:	0.865
LogD:	1.035
LogS:	-1.643
# Rotatable Bonds:	0
TPSA:	63.6
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.516
Synthetic Accessibility Score:	4.689
Fsp3:	0.714
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:	-4.88
MDCK Permeability:	7.659124094061553e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.673
Human Intestinal Absorption (HIA):	0.041
20% Bioavailability (F20%):	0.058
30% Bioavailability (F30%):	0.007

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.744
Plasma Protein Binding (PPB):	47.05280303955078%
Volume Distribution (VD):	0.529
Pgp-substrate:	66.37427520751953%

ADMET: Metabolism

CYP1A2-inhibitor:	0.048
CYP1A2-substrate:	0.124
CYP2C19-inhibitor:	0.017
CYP2C19-substrate:	0.697
CYP2C9-inhibitor:	0.004
CYP2C9-substrate:	0.076
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.193
CYP3A4-inhibitor:	0.023
CYP3A4-substrate:	0.211

ADMET: Excretion

Clearance (CL):	10.783
Half-life (T1/2):	0.706

ADMET: Toxicity

hERG Blockers:	0.032
Human Hepatotoxicity (H-HT):	0.807
Drug-inuced Liver Injury (DILI):	0.385
AMES Toxicity:	0.021
Rat Oral Acute Toxicity:	0.209
Maximum Recommended Daily Dose:	0.196
Skin Sensitization:	0.05
Carcinogencity:	0.205
Eye Corrosion:	0.01
Eye Irritation:	0.039
Respiratory Toxicity:	0.201

Download Data

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

Natural Product: NPC51499

Natural Product ID:	NPC51499
*Common Name:**	16-Epi-Scalarolbutenolide
IUPAC Name:	[(4S,5aS,5bR,7aS,11aS,11bR,13R,13aR,13bS)-13-hydroxy-5b,8,8,11a,13a-pentamethyl-2-oxo-5,5a,6,7,7a,9,10,11,11b,12,13,13b-dodecahydro-4H-phenanthro[1,2-g][1]benzofuran-4-yl] acetate
Synonyms:	16-Epi-Scalarolbutenolide
Standard InCHIKey:	NUXDYAGOJZSDBF-ZWRXBZFVSA-N
Standard InCHI:	InChI=1S/C27H40O5/c1-15(28)31-17-13-20-26(5)11-8-18-24(2,3)9-7-10-25(18,4)19(26)14-21(29)27(20,6)23-16(17)12-22(30)32-23/h12,17-21,23,29H,7-11,13-14H2,1-6H3/t17-,18-,19+,20-,21+,23-,25-,26+,27+/m0/s1
SMILES:	CC(=O)O[C@H]1C[C@@H]2[C@]([C@@H]3C1=CC(=O)O3)(C)[C@H](O)C[C@H]1[C@@]2(C)CC[C@@H]2[C@]1(C)CCCC2(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL476919
PubChem CID:	21600071
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001125] Steroid lactones

*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
NPO33333	hyrtios erecta	Species	Thorectidae	Eukaryota	n.a.	Red Sea	n.a.	PMID[11809054]
NPO33333	hyrtios erecta	Species	Thorectidae	Eukaryota	n.a.	Indian Ocean	n.a.	PMID[16124771]
NPO33333	hyrtios erecta	Species	Thorectidae	Eukaryota	n.a.	Red Sea	n.a.	PMID[16378375]
NPO25507	Spongia agaricina	Species	Spongiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[9548857]
NPO33333	hyrtios erecta	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[9584401]
NPO33333	hyrtios erecta	Species	Thorectidae	Eukaryota	n.a.	Maldives	n.a.	PMID[9873492]
NPO25507	Spongia agaricina	Species	Spongiidae	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	4
Others	1

Activity Type	# Activity
Cell Line	4
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	IC50	=	5.0	ug.mL-1	PMID[519471]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	5.0	ug.mL-1	PMID[519471]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	5.0	ug.mL-1	PMID[519471]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	IC50	=	5.0	ug.mL-1	PMID[519471]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	Inhibition	=	40.0	%	PMID[519470]

☑ 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 NPC51499 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	207
0.1-0.2	1416
0.2-0.3	4427
0.3-0.4	8720
0.4-0.5	13505
0.5-0.6	6418
0.6-0.7	5159
0.7-0.8	2563
0.8-0.85	234
0.85-0.9	43
0.9-0.95	2
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.989	High Similarity	NPC275086
0.989	High Similarity	NPC325229
0.914	High Similarity	NPC276110
0.9072	High Similarity	NPC97487
0.9072	High Similarity	NPC196471
0.9072	High Similarity	NPC189588
0.9072	High Similarity	NPC10232
0.9072	High Similarity	NPC187302
0.9072	High Similarity	NPC45897
0.9032	High Similarity	NPC105490
0.8925	High Similarity	NPC7349
0.8913	High Similarity	NPC78973
0.8889	High Similarity	NPC131813
0.8866	High Similarity	NPC11974
0.8866	High Similarity	NPC268829
0.8866	High Similarity	NPC247701
0.8866	High Similarity	NPC295110
0.8866	High Similarity	NPC25177
0.8866	High Similarity	NPC222875
0.8854	High Similarity	NPC278673
0.8817	High Similarity	NPC329842
0.8812	High Similarity	NPC475030
0.88	High Similarity	NPC471205
0.8778	High Similarity	NPC474013
0.8763	High Similarity	NPC477716
0.8763	High Similarity	NPC38855
0.8763	High Similarity	NPC251680
0.8763	High Similarity	NPC477721
0.875	High Similarity	NPC477719
0.875	High Similarity	NPC477718
0.87	High Similarity	NPC220217
0.87	High Similarity	NPC119855
0.87	High Similarity	NPC51719
0.8687	High Similarity	NPC281378
0.8687	High Similarity	NPC160583
0.8673	High Similarity	NPC477717
0.8614	High Similarity	NPC473586
0.8586	High Similarity	NPC475038
0.8586	High Similarity	NPC165250
0.8586	High Similarity	NPC476081
0.8586	High Similarity	NPC109195
0.8571	High Similarity	NPC161527
0.8571	High Similarity	NPC477968
0.8571	High Similarity	NPC228251
0.8571	High Similarity	NPC474190
0.8571	High Similarity	NPC20113
0.8571	High Similarity	NPC324841
0.8571	High Similarity	NPC477971
0.8571	High Similarity	NPC477972
0.8571	High Similarity	NPC219285
0.8544	High Similarity	NPC177047
0.8529	High Similarity	NPC475263
0.8526	High Similarity	NPC472641
0.8526	High Similarity	NPC472640
0.8515	High Similarity	NPC186668
0.8515	High Similarity	NPC88349
0.8515	High Similarity	NPC471206
0.85	High Similarity	NPC120321
0.85	High Similarity	NPC120009
0.85	High Similarity	NPC472821
0.8485	Intermediate Similarity	NPC235920
0.8485	Intermediate Similarity	NPC96784
0.8485	Intermediate Similarity	NPC471412
0.8485	Intermediate Similarity	NPC473160
0.8485	Intermediate Similarity	NPC472554
0.8469	Intermediate Similarity	NPC218107
0.8454	Intermediate Similarity	NPC234993
0.8454	Intermediate Similarity	NPC134072
0.8454	Intermediate Similarity	NPC194132
0.8454	Intermediate Similarity	NPC165632
0.8438	Intermediate Similarity	NPC140277
0.8438	Intermediate Similarity	NPC477722
0.8431	Intermediate Similarity	NPC475074
0.8431	Intermediate Similarity	NPC122816
0.8421	Intermediate Similarity	NPC234335
0.8421	Intermediate Similarity	NPC130840
0.8421	Intermediate Similarity	NPC41239
0.84	Intermediate Similarity	NPC258547
0.84	Intermediate Similarity	NPC11956
0.84	Intermediate Similarity	NPC273668
0.84	Intermediate Similarity	NPC283343
0.84	Intermediate Similarity	NPC472552
0.8387	Intermediate Similarity	NPC166857
0.8384	Intermediate Similarity	NPC476767
0.8384	Intermediate Similarity	NPC471413
0.8384	Intermediate Similarity	NPC16601
0.8367	Intermediate Similarity	NPC476878
0.8367	Intermediate Similarity	NPC476879
0.8352	Intermediate Similarity	NPC311070
0.835	Intermediate Similarity	NPC38948
0.835	Intermediate Similarity	NPC275539
0.835	Intermediate Similarity	NPC304276
0.835	Intermediate Similarity	NPC189075
0.835	Intermediate Similarity	NPC137462
0.8333	Intermediate Similarity	NPC139692
0.8333	Intermediate Similarity	NPC152778
0.8333	Intermediate Similarity	NPC472812
0.8333	Intermediate Similarity	NPC162615
0.8333	Intermediate Similarity	NPC110022
0.8333	Intermediate Similarity	NPC34768
0.8333	Intermediate Similarity	NPC53555
0.8333	Intermediate Similarity	NPC205034
0.8317	Intermediate Similarity	NPC23584
0.8317	Intermediate Similarity	NPC478057
0.8317	Intermediate Similarity	NPC112009
0.8317	Intermediate Similarity	NPC474822
0.8317	Intermediate Similarity	NPC471938
0.8316	Intermediate Similarity	NPC472642
0.8316	Intermediate Similarity	NPC221111
0.8316	Intermediate Similarity	NPC280149
0.8302	Intermediate Similarity	NPC171126
0.83	Intermediate Similarity	NPC475617
0.8298	Intermediate Similarity	NPC93411
0.8298	Intermediate Similarity	NPC106332
0.8283	Intermediate Similarity	NPC477876
0.8283	Intermediate Similarity	NPC477875
0.828	Intermediate Similarity	NPC471219
0.8269	Intermediate Similarity	NPC476759
0.8269	Intermediate Similarity	NPC206618
0.8265	Intermediate Similarity	NPC475380
0.8265	Intermediate Similarity	NPC209297
0.8265	Intermediate Similarity	NPC16967
0.8261	Intermediate Similarity	NPC32223
0.8261	Intermediate Similarity	NPC299963
0.8261	Intermediate Similarity	NPC102048
0.8252	Intermediate Similarity	NPC110496
0.8252	Intermediate Similarity	NPC67321
0.8252	Intermediate Similarity	NPC179380
0.8252	Intermediate Similarity	NPC187435
0.8252	Intermediate Similarity	NPC302788
0.8247	Intermediate Similarity	NPC3359
0.8247	Intermediate Similarity	NPC469697
0.8247	Intermediate Similarity	NPC57117
0.8247	Intermediate Similarity	NPC91010
0.8247	Intermediate Similarity	NPC201725
0.8241	Intermediate Similarity	NPC474418
0.8241	Intermediate Similarity	NPC84987
0.8241	Intermediate Similarity	NPC99728
0.8241	Intermediate Similarity	NPC157376
0.8241	Intermediate Similarity	NPC471355
0.8241	Intermediate Similarity	NPC196429
0.8241	Intermediate Similarity	NPC473852
0.8241	Intermediate Similarity	NPC471354
0.8241	Intermediate Similarity	NPC244402
0.8241	Intermediate Similarity	NPC471351
0.8241	Intermediate Similarity	NPC243196
0.8241	Intermediate Similarity	NPC50305
0.8241	Intermediate Similarity	NPC471353
0.8241	Intermediate Similarity	NPC27507
0.8241	Intermediate Similarity	NPC142066
0.8241	Intermediate Similarity	NPC309034
0.8241	Intermediate Similarity	NPC77319
0.8241	Intermediate Similarity	NPC34390
0.8241	Intermediate Similarity	NPC158344
0.8241	Intermediate Similarity	NPC87250
0.8235	Intermediate Similarity	NPC471937
0.8229	Intermediate Similarity	NPC72845
0.8229	Intermediate Similarity	NPC477574
0.8229	Intermediate Similarity	NPC472811
0.8224	Intermediate Similarity	NPC69576
0.8224	Intermediate Similarity	NPC471633
0.8224	Intermediate Similarity	NPC31354
0.8224	Intermediate Similarity	NPC84949
0.8222	Intermediate Similarity	NPC469802
0.8218	Intermediate Similarity	NPC162973
0.8218	Intermediate Similarity	NPC476890
0.8218	Intermediate Similarity	NPC475344
0.8218	Intermediate Similarity	NPC472815
0.8218	Intermediate Similarity	NPC471914
0.8218	Intermediate Similarity	NPC476769
0.8218	Intermediate Similarity	NPC476471
0.8211	Intermediate Similarity	NPC314727
0.8211	Intermediate Similarity	NPC170633
0.8211	Intermediate Similarity	NPC261320
0.8211	Intermediate Similarity	NPC246028
0.8208	Intermediate Similarity	NPC4573
0.8208	Intermediate Similarity	NPC470063
0.8208	Intermediate Similarity	NPC44537
0.82	Intermediate Similarity	NPC117685
0.82	Intermediate Similarity	NPC201406
0.82	Intermediate Similarity	NPC254567
0.82	Intermediate Similarity	NPC47024
0.82	Intermediate Similarity	NPC474571
0.8191	Intermediate Similarity	NPC471796
0.819	Intermediate Similarity	NPC12795
0.819	Intermediate Similarity	NPC103491
0.8182	Intermediate Similarity	NPC311241
0.8182	Intermediate Similarity	NPC224356
0.8182	Intermediate Similarity	NPC132753
0.8182	Intermediate Similarity	NPC100912
0.8182	Intermediate Similarity	NPC97867
0.8182	Intermediate Similarity	NPC475446
0.8182	Intermediate Similarity	NPC121402
0.8182	Intermediate Similarity	NPC175351
0.8182	Intermediate Similarity	NPC231751
0.8182	Intermediate Similarity	NPC151681
0.8173	Intermediate Similarity	NPC325054
0.8173	Intermediate Similarity	NPC476765
0.8173	Intermediate Similarity	NPC50124
0.8173	Intermediate Similarity	NPC306265

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 NPC51499 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	174
0.1-0.2	1567
0.2-0.3	3911
0.3-0.4	2317
0.4-0.5	741
0.5-0.6	245
0.6-0.7	164
0.7-0.8	25
0.8-0.85	6
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8854	High Similarity	NPD7638	Approved
0.8763	High Similarity	NPD7639	Approved
0.8763	High Similarity	NPD7640	Approved
0.8165	Intermediate Similarity	NPD7327	Approved
0.8165	Intermediate Similarity	NPD7328	Approved
0.8091	Intermediate Similarity	NPD7516	Approved
0.8039	Intermediate Similarity	NPD7632	Discontinued
0.7946	Intermediate Similarity	NPD8335	Approved
0.7946	Intermediate Similarity	NPD8380	Approved
0.7946	Intermediate Similarity	NPD8379	Approved
0.7946	Intermediate Similarity	NPD8296	Approved
0.7946	Intermediate Similarity	NPD8378	Approved
0.7879	Intermediate Similarity	NPD7748	Approved
0.7857	Intermediate Similarity	NPD8294	Approved
0.7857	Intermediate Similarity	NPD7515	Phase 2
0.7857	Intermediate Similarity	NPD8377	Approved
0.7788	Intermediate Similarity	NPD8033	Approved
0.7757	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7745	Intermediate Similarity	NPD4225	Approved
0.7717	Intermediate Similarity	NPD7645	Phase 2
0.7664	Intermediate Similarity	NPD6686	Approved
0.7647	Intermediate Similarity	NPD7902	Approved
0.7523	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7521	Intermediate Similarity	NPD7507	Approved
0.7479	Intermediate Similarity	NPD7319	Approved
0.7429	Intermediate Similarity	NPD5344	Discontinued
0.7353	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD7900	Approved
0.7328	Intermediate Similarity	NPD7503	Approved
0.7292	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7281	Intermediate Similarity	NPD7115	Discovery
0.7263	Intermediate Similarity	NPD7525	Registered
0.7248	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7245	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD6648	Approved
0.7157	Intermediate Similarity	NPD7637	Suspended
0.7157	Intermediate Similarity	NPD8035	Phase 2
0.7157	Intermediate Similarity	NPD8034	Phase 2
0.7156	Intermediate Similarity	NPD7128	Approved
0.7156	Intermediate Similarity	NPD5739	Approved
0.7156	Intermediate Similarity	NPD6675	Approved
0.7156	Intermediate Similarity	NPD6402	Approved
0.7143	Intermediate Similarity	NPD6400	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD6051	Approved
0.7041	Intermediate Similarity	NPD6695	Phase 3
0.703	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD6881	Approved
0.7027	Intermediate Similarity	NPD7320	Approved
0.7027	Intermediate Similarity	NPD6899	Approved
0.7	Intermediate Similarity	NPD3618	Phase 1
0.6981	Remote Similarity	NPD6084	Phase 2
0.6981	Remote Similarity	NPD6083	Phase 2
0.697	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD6372	Approved
0.6964	Remote Similarity	NPD6373	Approved
0.6961	Remote Similarity	NPD5328	Approved
0.6937	Remote Similarity	NPD6412	Phase 2
0.6937	Remote Similarity	NPD5701	Approved
0.6937	Remote Similarity	NPD5697	Approved
0.6923	Remote Similarity	NPD6399	Phase 3
0.6917	Remote Similarity	NPD8328	Phase 3
0.6903	Remote Similarity	NPD7290	Approved
0.6903	Remote Similarity	NPD7102	Approved
0.6903	Remote Similarity	NPD6883	Approved
0.6875	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.687	Remote Similarity	NPD8133	Approved
0.6842	Remote Similarity	NPD6650	Approved
0.6842	Remote Similarity	NPD6869	Approved
0.6842	Remote Similarity	NPD6649	Approved
0.6842	Remote Similarity	NPD6847	Approved
0.6842	Remote Similarity	NPD8130	Phase 1
0.6842	Remote Similarity	NPD6617	Approved
0.6832	Remote Similarity	NPD6684	Approved
0.6832	Remote Similarity	NPD7334	Approved
0.6832	Remote Similarity	NPD6409	Approved
0.6832	Remote Similarity	NPD7521	Approved
0.6832	Remote Similarity	NPD7146	Approved
0.6832	Remote Similarity	NPD5330	Approved
0.6827	Remote Similarity	NPD6079	Approved
0.6814	Remote Similarity	NPD6014	Approved
0.6814	Remote Similarity	NPD6013	Approved
0.6814	Remote Similarity	NPD6012	Approved
0.6804	Remote Similarity	NPD6929	Approved
0.6783	Remote Similarity	NPD8297	Approved
0.6783	Remote Similarity	NPD6882	Approved
0.6783	Remote Similarity	NPD6053	Discontinued
0.6765	Remote Similarity	NPD7750	Discontinued
0.6765	Remote Similarity	NPD7524	Approved
0.6737	Remote Similarity	NPD6942	Approved
0.6737	Remote Similarity	NPD7339	Approved
0.6735	Remote Similarity	NPD6930	Phase 2
0.6735	Remote Similarity	NPD6931	Approved
0.6733	Remote Similarity	NPD1694	Approved
0.6731	Remote Similarity	NPD6698	Approved
0.6731	Remote Similarity	NPD7838	Discovery
0.6731	Remote Similarity	NPD46	Approved
0.6726	Remote Similarity	NPD6011	Approved
0.6724	Remote Similarity	NPD4632	Approved
0.6699	Remote Similarity	NPD6903	Approved
0.6699	Remote Similarity	NPD5737	Approved
0.6699	Remote Similarity	NPD6672	Approved
0.6696	Remote Similarity	NPD6008	Approved
0.6696	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD7736	Approved
0.6667	Remote Similarity	NPD4755	Approved
0.6667	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6319	Approved
0.6667	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD5695	Phase 3
0.6634	Remote Similarity	NPD4786	Approved
0.6634	Remote Similarity	NPD3665	Phase 1
0.6634	Remote Similarity	NPD3666	Approved
0.6634	Remote Similarity	NPD3133	Approved
0.6606	Remote Similarity	NPD5696	Approved
0.6604	Remote Similarity	NPD5778	Approved
0.6604	Remote Similarity	NPD5779	Approved
0.6604	Remote Similarity	NPD4202	Approved
0.6602	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6602	Remote Similarity	NPD3573	Approved
0.66	Remote Similarity	NPD3667	Approved
0.6598	Remote Similarity	NPD5776	Phase 2
0.6598	Remote Similarity	NPD6925	Approved
0.6585	Remote Similarity	NPD7492	Approved
0.6577	Remote Similarity	NPD5211	Phase 2
0.6574	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD5222	Approved
0.6574	Remote Similarity	NPD4697	Phase 3
0.6574	Remote Similarity	NPD5221	Approved
0.6566	Remote Similarity	NPD7514	Phase 3
0.6566	Remote Similarity	NPD7332	Phase 2
0.6555	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6555	Remote Similarity	NPD6009	Approved
0.6545	Remote Similarity	NPD4700	Approved
0.6545	Remote Similarity	NPD4696	Approved
0.6545	Remote Similarity	NPD5285	Approved
0.6545	Remote Similarity	NPD5286	Approved
0.6532	Remote Similarity	NPD6616	Approved
0.6531	Remote Similarity	NPD6697	Approved
0.6531	Remote Similarity	NPD6118	Approved
0.6531	Remote Similarity	NPD6115	Approved
0.6531	Remote Similarity	NPD6114	Approved
0.6531	Remote Similarity	NPD7145	Approved
0.6529	Remote Similarity	NPD6059	Approved
0.6529	Remote Similarity	NPD6054	Approved
0.6514	Remote Similarity	NPD5173	Approved
0.6509	Remote Similarity	NPD7087	Discontinued
0.6509	Remote Similarity	NPD5693	Phase 1
0.6509	Remote Similarity	NPD6411	Approved
0.6504	Remote Similarity	NPD7604	Phase 2
0.65	Remote Similarity	NPD6902	Approved
0.6481	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.648	Remote Similarity	NPD7078	Approved
0.648	Remote Similarity	NPD8293	Discontinued
0.6476	Remote Similarity	NPD4753	Phase 2
0.6476	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6475	Remote Similarity	NPD5983	Phase 2
0.6471	Remote Similarity	NPD6274	Approved
0.6471	Remote Similarity	NPD6868	Approved
0.646	Remote Similarity	NPD5141	Approved
0.6446	Remote Similarity	NPD7101	Approved
0.6446	Remote Similarity	NPD7100	Approved
0.6429	Remote Similarity	NPD5226	Approved
0.6429	Remote Similarity	NPD6932	Approved
0.6429	Remote Similarity	NPD5224	Approved
0.6429	Remote Similarity	NPD5225	Approved
0.6429	Remote Similarity	NPD4633	Approved
0.6423	Remote Similarity	NPD6370	Approved
0.6408	Remote Similarity	NPD6893	Approved
0.64	Remote Similarity	NPD6336	Discontinued
0.6372	Remote Similarity	NPD5174	Approved
0.6372	Remote Similarity	NPD5175	Approved
0.6364	Remote Similarity	NPD6335	Approved
0.635	Remote Similarity	NPD7625	Phase 1
0.6341	Remote Similarity	NPD6909	Approved
0.6341	Remote Similarity	NPD6908	Approved
0.6341	Remote Similarity	NPD6015	Approved
0.6341	Remote Similarity	NPD6016	Approved
0.6339	Remote Similarity	NPD5223	Approved
0.6339	Remote Similarity	NPD4159	Approved
0.6337	Remote Similarity	NPD6898	Phase 1
0.6327	Remote Similarity	NPD6117	Approved
0.6325	Remote Similarity	NPD4634	Approved
0.6325	Remote Similarity	NPD6371	Approved
0.6321	Remote Similarity	NPD6101	Approved
0.6321	Remote Similarity	NPD6080	Approved
0.6321	Remote Similarity	NPD6673	Approved
0.6321	Remote Similarity	NPD6904	Approved
0.6321	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6306	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6306	Remote Similarity	NPD5290	Discontinued
0.63	Remote Similarity	NPD6683	Phase 2
0.63	Remote Similarity	NPD4195	Approved
0.629	Remote Similarity	NPD5988	Approved
0.6289	Remote Similarity	NPD6924	Approved
0.6289	Remote Similarity	NPD6926	Approved
0.6281	Remote Similarity	NPD6317	Approved
0.6263	Remote Similarity	NPD6116	Phase 1
0.6262	Remote Similarity	NPD5785	Approved
0.6261	Remote Similarity	NPD4767	Approved
0.6261	Remote Similarity	NPD4768	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