NPASS Compound

Structure

CID325229 OpenBabel06191716182D 32 36 0 0 1 0 0 0 0 0999 V2000 0.6957 -3.3145 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7599 -1.9461 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2544 -1.0718 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1942 -2.4498 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2187 0.5172 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6622 -0.9884 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9072 -3.4082 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9058 -0.4856 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7505 -2.9207 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0634 -2.9217 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0623 0.0014 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8424 1.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3746 0.9749 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3754 -1.9481 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5858 -2.9178 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6866 0.9744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5304 1.4619 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.9061 -1.4601 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2193 -1.4606 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3749 0.0010 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5313 -1.4611 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0003 0.9739 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6868 0.0005 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.7499 -1.9467 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0628 -1.9476 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.2190 -0.4861 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5310 -0.4865 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.3744 -3.4904 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5301 2.4652 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8666 1.4734 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6874 -1.9486 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 29 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 31 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:	444.29
Volume:	468.808
LogP:	4.318
LogD:	3.819
LogS:	-4.239
# Rotatable Bonds:	2
TPSA:	79.9
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.529
Synthetic Accessibility Score:	4.95
Fsp3:	0.815
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.919
MDCK Permeability:	2.5229513994418085e-05
Pgp-inhibitor:	0.922
Pgp-substrate:	0.2
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.061
30% Bioavailability (F30%):	0.95

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.64
Plasma Protein Binding (PPB):	93.04772186279297%
Volume Distribution (VD):	1.029
Pgp-substrate:	12.432646751403809%

ADMET: Metabolism

CYP1A2-inhibitor:	0.032
CYP1A2-substrate:	0.171
CYP2C19-inhibitor:	0.032
CYP2C19-substrate:	0.723
CYP2C9-inhibitor:	0.255
CYP2C9-substrate:	0.656
CYP2D6-inhibitor:	0.025
CYP2D6-substrate:	0.485
CYP3A4-inhibitor:	0.214
CYP3A4-substrate:	0.301

ADMET: Excretion

Clearance (CL):	6.147
Half-life (T1/2):	0.275

ADMET: Toxicity

hERG Blockers:	0.021
Human Hepatotoxicity (H-HT):	0.159
Drug-inuced Liver Injury (DILI):	0.143
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.315
Maximum Recommended Daily Dose:	0.957
Skin Sensitization:	0.281
Carcinogencity:	0.123
Eye Corrosion:	0.004
Eye Irritation:	0.103
Respiratory Toxicity:	0.966

Download Data

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

Natural Product: NPC325229

Natural Product ID:	NPC325229
*Common Name:**	12-O-Acetyl-16-O-Deacetyl-16-Epi-Scalarobutenolide
IUPAC Name:	[(4S,5aS,5bR,7aS,11aS,11bR,13R,13aR,13bS)-4-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-13-yl] acetate
Synonyms:
Standard InCHIKey:	TUHLUXIESILORF-ZWRXBZFVSA-N
Standard InCHI:	InChI=1S/C27H40O5/c1-15(28)31-21-14-19-25(4)10-7-9-24(2,3)18(25)8-11-26(19,5)20-13-17(29)16-12-22(30)32-23(16)27(20,21)6/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]3[C@@]1(C)[C@H]1OC(=O)C=C1[C@H](C3)O)(C)CC[C@@H]1[C@]2(C)CCCC1(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL463374
PubChem CID:	10765720
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
NPO5239	Hyrtios erecta	Species	Thorectidae	Eukaryota	n.a.	Okinawan	n.a.	PMID[11076554]
NPO5239	Hyrtios erecta	Species	Thorectidae	Eukaryota	n.a.	red sea	n.a.	PMID[16180827]
NPO5239	Hyrtios erecta	Species	Thorectidae	Eukaryota	n.a.	Red Sea	n.a.	PMID[17190441]
NPO5239	Hyrtios erecta	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[3572416]
NPO5239	Hyrtios erecta	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[8778242]
NPO5239	Hyrtios erecta	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[9461648]
NPO5239	Hyrtios erecta	Species	Thorectidae	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
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	IC50	=	2.1	ug.mL-1	PMID[520003]

☑ 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 NPC325229 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	204
0.1-0.2	1431
0.2-0.3	4348
0.3-0.4	8359
0.4-0.5	13795
0.5-0.6	6593
0.6-0.7	5171
0.7-0.8	2528
0.8-0.85	233
0.85-0.9	27
0.9-0.95	5
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC275086
0.989	High Similarity	NPC51499
0.9043	High Similarity	NPC276110
0.9022	High Similarity	NPC78973
0.898	High Similarity	NPC187302
0.898	High Similarity	NPC189588
0.898	High Similarity	NPC10232
0.898	High Similarity	NPC97487
0.898	High Similarity	NPC196471
0.898	High Similarity	NPC45897
0.8936	High Similarity	NPC105490
0.8925	High Similarity	NPC329842
0.89	High Similarity	NPC471205
0.8866	High Similarity	NPC477721
0.8866	High Similarity	NPC251680
0.8866	High Similarity	NPC477716
0.8866	High Similarity	NPC38855
0.8854	High Similarity	NPC477719
0.8854	High Similarity	NPC477718
0.883	High Similarity	NPC7349
0.8791	High Similarity	NPC131813
0.8776	High Similarity	NPC25177
0.8776	High Similarity	NPC222875
0.8776	High Similarity	NPC295110
0.8776	High Similarity	NPC11974
0.8776	High Similarity	NPC477717
0.8776	High Similarity	NPC247701
0.8776	High Similarity	NPC268829
0.8763	High Similarity	NPC278673
0.8725	High Similarity	NPC475030
0.8687	High Similarity	NPC109195
0.8687	High Similarity	NPC475038
0.8681	High Similarity	NPC474013
0.8673	High Similarity	NPC324841
0.8632	High Similarity	NPC472640
0.8632	High Similarity	NPC472641
0.8614	High Similarity	NPC119855
0.8614	High Similarity	NPC220217
0.8614	High Similarity	NPC51719
0.86	High Similarity	NPC281378
0.86	High Similarity	NPC160583
0.8586	High Similarity	NPC235920
0.8586	High Similarity	NPC96784
0.8571	High Similarity	NPC218107
0.8557	High Similarity	NPC165632
0.8557	High Similarity	NPC234993
0.8557	High Similarity	NPC134072
0.8529	High Similarity	NPC473586
0.8529	High Similarity	NPC122816
0.8526	High Similarity	NPC41239
0.85	High Similarity	NPC476081
0.85	High Similarity	NPC165250
0.8495	Intermediate Similarity	NPC166857
0.8485	Intermediate Similarity	NPC476767
0.8485	Intermediate Similarity	NPC16601
0.8485	Intermediate Similarity	NPC219285
0.8485	Intermediate Similarity	NPC477968
0.8485	Intermediate Similarity	NPC161527
0.8485	Intermediate Similarity	NPC477972
0.8485	Intermediate Similarity	NPC477971
0.8485	Intermediate Similarity	NPC20113
0.8485	Intermediate Similarity	NPC228251
0.8485	Intermediate Similarity	NPC474190
0.8462	Intermediate Similarity	NPC177047
0.8462	Intermediate Similarity	NPC311070
0.8447	Intermediate Similarity	NPC38948
0.8447	Intermediate Similarity	NPC475263
0.8438	Intermediate Similarity	NPC472812
0.8438	Intermediate Similarity	NPC53555
0.8431	Intermediate Similarity	NPC186668
0.8431	Intermediate Similarity	NPC88349
0.8431	Intermediate Similarity	NPC471206
0.8421	Intermediate Similarity	NPC472642
0.8416	Intermediate Similarity	NPC120321
0.8416	Intermediate Similarity	NPC478057
0.8416	Intermediate Similarity	NPC120009
0.8416	Intermediate Similarity	NPC474822
0.8416	Intermediate Similarity	NPC472821
0.8416	Intermediate Similarity	NPC471938
0.84	Intermediate Similarity	NPC472554
0.84	Intermediate Similarity	NPC473160
0.84	Intermediate Similarity	NPC471412
0.837	Intermediate Similarity	NPC102048
0.8367	Intermediate Similarity	NPC194132
0.8365	Intermediate Similarity	NPC206618
0.8351	Intermediate Similarity	NPC57117
0.8351	Intermediate Similarity	NPC477722
0.8351	Intermediate Similarity	NPC140277
0.8351	Intermediate Similarity	NPC469697
0.835	Intermediate Similarity	NPC67321
0.835	Intermediate Similarity	NPC475074
0.835	Intermediate Similarity	NPC187435
0.8333	Intermediate Similarity	NPC130840
0.8333	Intermediate Similarity	NPC234335
0.8333	Intermediate Similarity	NPC472811
0.8333	Intermediate Similarity	NPC471937
0.8317	Intermediate Similarity	NPC471914
0.8317	Intermediate Similarity	NPC283343
0.8317	Intermediate Similarity	NPC258547
0.8317	Intermediate Similarity	NPC273668
0.8317	Intermediate Similarity	NPC11956
0.8317	Intermediate Similarity	NPC472815
0.8317	Intermediate Similarity	NPC472552
0.8316	Intermediate Similarity	NPC170633
0.8316	Intermediate Similarity	NPC314727
0.8316	Intermediate Similarity	NPC246028
0.83	Intermediate Similarity	NPC471413
0.8283	Intermediate Similarity	NPC476878
0.8283	Intermediate Similarity	NPC476879
0.8269	Intermediate Similarity	NPC306265
0.8269	Intermediate Similarity	NPC88701
0.8269	Intermediate Similarity	NPC325054
0.8269	Intermediate Similarity	NPC304276
0.8269	Intermediate Similarity	NPC189075
0.8269	Intermediate Similarity	NPC137462
0.8269	Intermediate Similarity	NPC476765
0.8269	Intermediate Similarity	NPC50124
0.8269	Intermediate Similarity	NPC275539
0.8265	Intermediate Similarity	NPC471915
0.8265	Intermediate Similarity	NPC472441
0.8265	Intermediate Similarity	NPC111273
0.8261	Intermediate Similarity	NPC42476
0.8261	Intermediate Similarity	NPC476927
0.8252	Intermediate Similarity	NPC34768
0.8252	Intermediate Similarity	NPC472818
0.8247	Intermediate Similarity	NPC110022
0.8247	Intermediate Similarity	NPC205034
0.8247	Intermediate Similarity	NPC162615
0.8247	Intermediate Similarity	NPC139692
0.8247	Intermediate Similarity	NPC152778
0.8242	Intermediate Similarity	NPC170303
0.8235	Intermediate Similarity	NPC112009
0.8235	Intermediate Similarity	NPC23584
0.8235	Intermediate Similarity	NPC473523
0.8235	Intermediate Similarity	NPC471208
0.8235	Intermediate Similarity	NPC95899
0.8229	Intermediate Similarity	NPC219937
0.8229	Intermediate Similarity	NPC220216
0.8229	Intermediate Similarity	NPC194485
0.8229	Intermediate Similarity	NPC280149
0.8229	Intermediate Similarity	NPC53890
0.8229	Intermediate Similarity	NPC221111
0.8229	Intermediate Similarity	NPC123252
0.8224	Intermediate Similarity	NPC171126
0.8218	Intermediate Similarity	NPC475617
0.8211	Intermediate Similarity	NPC472810
0.8211	Intermediate Similarity	NPC106332
0.8211	Intermediate Similarity	NPC472809
0.8211	Intermediate Similarity	NPC291665
0.8211	Intermediate Similarity	NPC93411
0.82	Intermediate Similarity	NPC477876
0.82	Intermediate Similarity	NPC247233
0.82	Intermediate Similarity	NPC477875
0.8191	Intermediate Similarity	NPC471219
0.819	Intermediate Similarity	NPC31522
0.819	Intermediate Similarity	NPC322912
0.819	Intermediate Similarity	NPC476759
0.8182	Intermediate Similarity	NPC209297
0.8182	Intermediate Similarity	NPC16967
0.8182	Intermediate Similarity	NPC54248
0.8182	Intermediate Similarity	NPC211810
0.8182	Intermediate Similarity	NPC276103
0.8182	Intermediate Similarity	NPC242848
0.8182	Intermediate Similarity	NPC202833
0.8182	Intermediate Similarity	NPC475380
0.8182	Intermediate Similarity	NPC162346
0.8182	Intermediate Similarity	NPC284194
0.8182	Intermediate Similarity	NPC221801
0.8182	Intermediate Similarity	NPC471765
0.8173	Intermediate Similarity	NPC472820
0.8173	Intermediate Similarity	NPC302788
0.8173	Intermediate Similarity	NPC179380
0.8173	Intermediate Similarity	NPC475781
0.8173	Intermediate Similarity	NPC110496
0.8172	Intermediate Similarity	NPC32223
0.8172	Intermediate Similarity	NPC299963
0.8165	Intermediate Similarity	NPC87250
0.8165	Intermediate Similarity	NPC471353
0.8165	Intermediate Similarity	NPC471354
0.8165	Intermediate Similarity	NPC309034
0.8165	Intermediate Similarity	NPC142066
0.8165	Intermediate Similarity	NPC157376
0.8165	Intermediate Similarity	NPC474418
0.8165	Intermediate Similarity	NPC473852
0.8165	Intermediate Similarity	NPC158344
0.8165	Intermediate Similarity	NPC243196
0.8165	Intermediate Similarity	NPC244402
0.8165	Intermediate Similarity	NPC471351
0.8165	Intermediate Similarity	NPC99728
0.8165	Intermediate Similarity	NPC196429
0.8165	Intermediate Similarity	NPC77319
0.8165	Intermediate Similarity	NPC84987
0.8165	Intermediate Similarity	NPC34390
0.8165	Intermediate Similarity	NPC471355
0.8165	Intermediate Similarity	NPC27507
0.8165	Intermediate Similarity	NPC50305
0.8163	Intermediate Similarity	NPC119562
0.8163	Intermediate Similarity	NPC91010
0.8163	Intermediate Similarity	NPC474922
0.8163	Intermediate Similarity	NPC279410

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 NPC325229 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	176
0.1-0.2	1588
0.2-0.3	3870
0.3-0.4	2306
0.4-0.5	773
0.5-0.6	253
0.6-0.7	154
0.7-0.8	24
0.8-0.85	4
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8866	High Similarity	NPD7640	Approved
0.8866	High Similarity	NPD7639	Approved
0.8763	High Similarity	NPD7638	Approved
0.8137	Intermediate Similarity	NPD7632	Discontinued
0.8091	Intermediate Similarity	NPD7328	Approved
0.8091	Intermediate Similarity	NPD7327	Approved
0.8018	Intermediate Similarity	NPD7516	Approved
0.7876	Intermediate Similarity	NPD8378	Approved
0.7876	Intermediate Similarity	NPD8335	Approved
0.7876	Intermediate Similarity	NPD8380	Approved
0.7876	Intermediate Similarity	NPD8379	Approved
0.7876	Intermediate Similarity	NPD8296	Approved
0.7843	Intermediate Similarity	NPD4225	Approved
0.78	Intermediate Similarity	NPD7748	Approved
0.7788	Intermediate Similarity	NPD8294	Approved
0.7788	Intermediate Similarity	NPD8377	Approved
0.7778	Intermediate Similarity	NPD7515	Phase 2
0.7719	Intermediate Similarity	NPD8033	Approved
0.7685	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7634	Intermediate Similarity	NPD7645	Phase 2
0.7593	Intermediate Similarity	NPD6686	Approved
0.7573	Intermediate Similarity	NPD7902	Approved
0.7524	Intermediate Similarity	NPD5344	Discontinued
0.7458	Intermediate Similarity	NPD7507	Approved
0.7455	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD7319	Approved
0.7368	Intermediate Similarity	NPD7115	Discovery
0.7282	Intermediate Similarity	NPD7900	Approved
0.7282	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7265	Intermediate Similarity	NPD7503	Approved
0.7264	Intermediate Similarity	NPD6648	Approved
0.7255	Intermediate Similarity	NPD7637	Suspended
0.7245	Intermediate Similarity	NPD6400	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD7525	Registered
0.7182	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6695	Phase 3
0.7091	Intermediate Similarity	NPD6675	Approved
0.7091	Intermediate Similarity	NPD6402	Approved
0.7091	Intermediate Similarity	NPD5739	Approved
0.7091	Intermediate Similarity	NPD7128	Approved
0.7087	Intermediate Similarity	NPD8034	Phase 2
0.7087	Intermediate Similarity	NPD8035	Phase 2
0.7071	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6051	Approved
0.6964	Remote Similarity	NPD7320	Approved
0.6964	Remote Similarity	NPD6899	Approved
0.6964	Remote Similarity	NPD6881	Approved
0.6961	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD3618	Phase 1
0.6916	Remote Similarity	NPD6083	Phase 2
0.6916	Remote Similarity	NPD6084	Phase 2
0.6907	Remote Similarity	NPD6929	Approved
0.6903	Remote Similarity	NPD6373	Approved
0.6903	Remote Similarity	NPD6372	Approved
0.6893	Remote Similarity	NPD5328	Approved
0.6875	Remote Similarity	NPD6412	Phase 2
0.6875	Remote Similarity	NPD5701	Approved
0.6875	Remote Similarity	NPD5697	Approved
0.6863	Remote Similarity	NPD7524	Approved
0.6863	Remote Similarity	NPD7750	Discontinued
0.686	Remote Similarity	NPD8328	Phase 3
0.6857	Remote Similarity	NPD6399	Phase 3
0.6842	Remote Similarity	NPD7290	Approved
0.6842	Remote Similarity	NPD7102	Approved
0.6842	Remote Similarity	NPD6883	Approved
0.6837	Remote Similarity	NPD6930	Phase 2
0.6837	Remote Similarity	NPD6931	Approved
0.6814	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.681	Remote Similarity	NPD8133	Approved
0.6783	Remote Similarity	NPD8130	Phase 1
0.6783	Remote Similarity	NPD6847	Approved
0.6783	Remote Similarity	NPD6650	Approved
0.6783	Remote Similarity	NPD6869	Approved
0.6783	Remote Similarity	NPD6617	Approved
0.6783	Remote Similarity	NPD6649	Approved
0.6765	Remote Similarity	NPD6684	Approved
0.6765	Remote Similarity	NPD7334	Approved
0.6765	Remote Similarity	NPD7146	Approved
0.6765	Remote Similarity	NPD6409	Approved
0.6765	Remote Similarity	NPD5330	Approved
0.6765	Remote Similarity	NPD7521	Approved
0.6762	Remote Similarity	NPD6079	Approved
0.6754	Remote Similarity	NPD6014	Approved
0.6754	Remote Similarity	NPD6012	Approved
0.6754	Remote Similarity	NPD6013	Approved
0.6724	Remote Similarity	NPD8297	Approved
0.6724	Remote Similarity	NPD6882	Approved
0.6724	Remote Similarity	NPD6053	Discontinued
0.6701	Remote Similarity	NPD6925	Approved
0.6701	Remote Similarity	NPD5776	Phase 2
0.6699	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD5779	Approved
0.6698	Remote Similarity	NPD5778	Approved
0.6667	Remote Similarity	NPD6698	Approved
0.6667	Remote Similarity	NPD46	Approved
0.6667	Remote Similarity	NPD5211	Phase 2
0.6667	Remote Similarity	NPD6942	Approved
0.6667	Remote Similarity	NPD7514	Phase 3
0.6667	Remote Similarity	NPD7332	Phase 2
0.6667	Remote Similarity	NPD7838	Discovery
0.6667	Remote Similarity	NPD6011	Approved
0.6667	Remote Similarity	NPD1694	Approved
0.6667	Remote Similarity	NPD4632	Approved
0.6667	Remote Similarity	NPD7339	Approved
0.664	Remote Similarity	NPD7736	Approved
0.6638	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6637	Remote Similarity	NPD6008	Approved
0.6635	Remote Similarity	NPD5737	Approved
0.6635	Remote Similarity	NPD6903	Approved
0.6635	Remote Similarity	NPD6672	Approved
0.6633	Remote Similarity	NPD7145	Approved
0.6612	Remote Similarity	NPD6319	Approved
0.6609	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD4755	Approved
0.6604	Remote Similarity	NPD7087	Discontinued
0.66	Remote Similarity	NPD6902	Approved
0.6598	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD5695	Phase 3
0.6569	Remote Similarity	NPD3133	Approved
0.6569	Remote Similarity	NPD4786	Approved
0.6569	Remote Similarity	NPD3666	Approved
0.6569	Remote Similarity	NPD3665	Phase 1
0.6549	Remote Similarity	NPD5141	Approved
0.6545	Remote Similarity	NPD5696	Approved
0.6542	Remote Similarity	NPD4202	Approved
0.6538	Remote Similarity	NPD3573	Approved
0.6535	Remote Similarity	NPD3667	Approved
0.6532	Remote Similarity	NPD7492	Approved
0.6514	Remote Similarity	NPD5221	Approved
0.6514	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD4697	Phase 3
0.6514	Remote Similarity	NPD5222	Approved
0.6505	Remote Similarity	NPD6893	Approved
0.65	Remote Similarity	NPD6009	Approved
0.65	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD4700	Approved
0.6486	Remote Similarity	NPD4696	Approved
0.6486	Remote Similarity	NPD5286	Approved
0.6486	Remote Similarity	NPD5285	Approved
0.648	Remote Similarity	NPD6616	Approved
0.6475	Remote Similarity	NPD6059	Approved
0.6475	Remote Similarity	NPD6054	Approved
0.6465	Remote Similarity	NPD6115	Approved
0.6465	Remote Similarity	NPD6697	Approved
0.6465	Remote Similarity	NPD6114	Approved
0.6465	Remote Similarity	NPD6118	Approved
0.6455	Remote Similarity	NPD5173	Approved
0.6452	Remote Similarity	NPD7604	Phase 2
0.6449	Remote Similarity	NPD5693	Phase 1
0.6449	Remote Similarity	NPD6411	Approved
0.6436	Remote Similarity	NPD6898	Phase 1
0.6429	Remote Similarity	NPD7078	Approved
0.6429	Remote Similarity	NPD8293	Discontinued
0.6423	Remote Similarity	NPD5983	Phase 2
0.6422	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6417	Remote Similarity	NPD6274	Approved
0.6417	Remote Similarity	NPD6868	Approved
0.6415	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD4753	Phase 2
0.641	Remote Similarity	NPD6371	Approved
0.6396	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6393	Remote Similarity	NPD7100	Approved
0.6393	Remote Similarity	NPD7101	Approved
0.6372	Remote Similarity	NPD5226	Approved
0.6372	Remote Similarity	NPD4633	Approved
0.6372	Remote Similarity	NPD5225	Approved
0.6372	Remote Similarity	NPD5224	Approved
0.6371	Remote Similarity	NPD6370	Approved
0.6364	Remote Similarity	NPD6932	Approved
0.6355	Remote Similarity	NPD5785	Approved
0.6349	Remote Similarity	NPD6336	Discontinued
0.6327	Remote Similarity	NPD8264	Approved
0.6316	Remote Similarity	NPD5174	Approved
0.6316	Remote Similarity	NPD5175	Approved
0.6311	Remote Similarity	NPD6335	Approved
0.6304	Remote Similarity	NPD7625	Phase 1
0.629	Remote Similarity	NPD8513	Phase 3
0.629	Remote Similarity	NPD8516	Approved
0.629	Remote Similarity	NPD6909	Approved
0.629	Remote Similarity	NPD6908	Approved
0.629	Remote Similarity	NPD8515	Approved
0.629	Remote Similarity	NPD6015	Approved
0.629	Remote Similarity	NPD8517	Approved
0.629	Remote Similarity	NPD6016	Approved
0.6286	Remote Similarity	NPD4623	Approved
0.6286	Remote Similarity	NPD4519	Discontinued
0.6283	Remote Similarity	NPD4159	Approved
0.6283	Remote Similarity	NPD5223	Approved
0.6271	Remote Similarity	NPD4634	Approved
0.6263	Remote Similarity	NPD6117	Approved
0.6262	Remote Similarity	NPD6101	Approved
0.6262	Remote Similarity	NPD6673	Approved
0.6262	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD6080	Approved
0.6262	Remote Similarity	NPD6904	Approved
0.625	Remote Similarity	NPD5290	Discontinued
0.624	Remote Similarity	NPD5988	Approved
0.6238	Remote Similarity	NPD4195	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