NPASS Compound

Structure

NPC199936 OpenBabel07101719152D 32 36 0 0 1 0 0 0 0 0999 V2000 1.6852 3.8919 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5279 0.4865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8426 -1.4595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.9459 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.9730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6852 -1.9459 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6852 0.9730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8426 -1.4595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8426 1.4595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6852 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8426 -0.4865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8426 2.4324 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3705 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5279 1.4595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3705 -2.9189 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6852 2.9189 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5279 -1.4595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5279 -0.4865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3705 -1.9459 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6852 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2131 -0.4865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5279 2.4324 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8426 1.4595 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.2131 -1.4595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6852 0.9730 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8426 -0.4865 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 0.9730 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2131 -3.4054 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0557 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3705 2.9189 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0557 -1.9459 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3 26 1 0 0 0 0 4 27 1 0 0 0 0 6 8 2 0 0 0 0 6 17 1 0 0 0 0 7 9 1 0 0 0 0 7 20 2 0 0 0 0 8 26 1 0 0 0 0 9 27 1 0 0 0 0 10 11 1 0 0 0 0 10 25 1 0 0 0 0 11 28 1 0 0 0 0 12 16 1 0 0 0 0 12 23 1 0 0 0 0 13 18 2 0 0 0 0 13 21 1 0 0 0 0 14 22 1 0 0 0 0 14 25 1 0 0 0 0 15 19 1 0 0 0 0 15 29 2 0 0 0 0 16 1 1 1 0 0 0 16 22 1 0 0 0 0 17 18 1 0 0 0 0 17 19 2 0 0 0 0 18 20 1 0 0 0 0 19 24 1 0 0 0 0 20 26 1 0 0 0 0 21 24 2 0 0 0 0 21 30 1 0 0 0 0 22 31 2 0 0 0 0 23 25 1 6 0 0 0 23 27 1 0 0 0 0 24 32 1 0 0 0 0 25 2 1 1 0 0 0 26 28 1 6 0 0 0 27 28 1 6 0 0 0 28 5 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	434.25
Volume:	466.767
LogP:	4.615
LogD:	3.609
LogS:	-4.559
# Rotatable Bonds:	1
TPSA:	74.6
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.322
Synthetic Accessibility Score:	5.356
Fsp3:	0.571
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.896
MDCK Permeability:	2.4004986698855646e-05
Pgp-inhibitor:	0.075
Pgp-substrate:	0.007
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.028

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.456
Plasma Protein Binding (PPB):	99.36675262451172%
Volume Distribution (VD):	1.583
Pgp-substrate:	1.8782532215118408%

ADMET: Metabolism

CYP1A2-inhibitor:	0.042
CYP1A2-substrate:	0.755
CYP2C19-inhibitor:	0.068
CYP2C19-substrate:	0.714
CYP2C9-inhibitor:	0.284
CYP2C9-substrate:	0.281
CYP2D6-inhibitor:	0.267
CYP2D6-substrate:	0.099
CYP3A4-inhibitor:	0.89
CYP3A4-substrate:	0.871

ADMET: Excretion

Clearance (CL):	15.29
Half-life (T1/2):	0.247

ADMET: Toxicity

hERG Blockers:	0.065
Human Hepatotoxicity (H-HT):	0.224
Drug-inuced Liver Injury (DILI):	0.077
AMES Toxicity:	0.198
Rat Oral Acute Toxicity:	0.773
Maximum Recommended Daily Dose:	0.953
Skin Sensitization:	0.178
Carcinogencity:	0.881
Eye Corrosion:	0.004
Eye Irritation:	0.19
Respiratory Toxicity:	0.958

Download Data

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

Natural Product: NPC199936

Natural Product ID:	NPC199936
*Common Name:**	23-Oxo-Isotingenone
IUPAC Name:	(6aS,6aS,6bS,8aS,11R,12aR)-2,3-dihydroxy-6a,6a,6b,8a,11-pentamethyl-10-oxo-8,9,11,12,12a,13-hexahydro-7H-picene-4-carbaldehyde
Synonyms:	23-Oxo-Isotingenone
Standard InCHIKey:	ZIHMKXOMCSCWJB-AHRBEJICSA-N
Standard InCHI:	InChI=1S/C28H34O4/c1-16-12-23-25(2,14-22(16)31)10-11-28(5)26(3)8-6-17-18(20(26)7-9-27(23,28)4)13-21(30)24(32)19(17)15-29/h6-8,13,15-16,23,30,32H,9-12,14H2,1-5H3/t16-,23-,25+,26-,27+,28-/m1/s1
SMILES:	C[C@@H]1C[C@@H]2[C@@](C)(CC[C@]3(C)[C@]4(C)C=Cc5c(cc(c(c5C=O)O)O)C4=CC[C@@]23C)CC1=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL454829
PubChem CID:	10788966
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000025] Phenanthrenes 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
NPO13212	Maytenus amazonica	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10096852]
NPO13212	Maytenus amazonica	Species	Celastraceae	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	5

Activity Type	# Activity
Cell Line	3
Individual Protein	1
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	IC50	=	10.0	ug.mL-1	PMID[451880]
NPT41	Individual Protein	Aldose reductase	Homo sapiens	IC50	=	25.0	ug.mL-1	PMID[451880]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	10.0	ug.mL-1	PMID[451880]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	10.0	ug.mL-1	PMID[451880]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	10.0	ug.mL-1	PMID[451880]

☑ 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 NPC199936 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	363
0.1-0.2	1472
0.2-0.3	3056
0.3-0.4	7676
0.4-0.5	10986
0.5-0.6	6975
0.6-0.7	9756
0.7-0.8	2272
0.8-0.85	123
0.85-0.9	14
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9137	High Similarity	NPC277559
0.911	High Similarity	NPC470037
0.9	High Similarity	NPC49911
0.8951	High Similarity	NPC184935
0.8904	High Similarity	NPC10842
0.8897	High Similarity	NPC470038
0.8803	High Similarity	NPC206207
0.8707	High Similarity	NPC476535
0.8681	High Similarity	NPC476534
0.8671	High Similarity	NPC141368
0.8662	High Similarity	NPC7464
0.8639	High Similarity	NPC68441
0.8592	High Similarity	NPC103082
0.8592	High Similarity	NPC153088
0.8582	High Similarity	NPC138472
0.8582	High Similarity	NPC111845
0.8582	High Similarity	NPC476282
0.8571	High Similarity	NPC243305
0.8571	High Similarity	NPC291001
0.8562	High Similarity	NPC471972
0.8562	High Similarity	NPC30846
0.8562	High Similarity	NPC469855
0.8562	High Similarity	NPC471971
0.8552	High Similarity	NPC470035
0.8552	High Similarity	NPC471853
0.8542	High Similarity	NPC289358
0.8542	High Similarity	NPC42384
0.8542	High Similarity	NPC28592
0.8542	High Similarity	NPC114333
0.8542	High Similarity	NPC5014
0.8542	High Similarity	NPC297797
0.8542	High Similarity	NPC473779
0.8542	High Similarity	NPC245760
0.8542	High Similarity	NPC149773
0.8542	High Similarity	NPC23667
0.8542	High Similarity	NPC91887
0.8542	High Similarity	NPC50615
0.8542	High Similarity	NPC473479
0.8542	High Similarity	NPC477849
0.8542	High Similarity	NPC469857
0.8542	High Similarity	NPC165191
0.8542	High Similarity	NPC51531
0.8542	High Similarity	NPC157284
0.8542	High Similarity	NPC46242
0.8483	Intermediate Similarity	NPC294330
0.8478	Intermediate Similarity	NPC71610
0.8477	Intermediate Similarity	NPC476532
0.8477	Intermediate Similarity	NPC474191
0.8462	Intermediate Similarity	NPC258502
0.8451	Intermediate Similarity	NPC294226
0.8446	Intermediate Similarity	NPC469854
0.8446	Intermediate Similarity	NPC469856
0.844	Intermediate Similarity	NPC244699
0.8435	Intermediate Similarity	NPC248068
0.8429	Intermediate Similarity	NPC474546
0.8425	Intermediate Similarity	NPC473527
0.8417	Intermediate Similarity	NPC471530
0.8414	Intermediate Similarity	NPC230811
0.8414	Intermediate Similarity	NPC471974
0.8414	Intermediate Similarity	NPC469681
0.8414	Intermediate Similarity	NPC61398
0.8414	Intermediate Similarity	NPC416
0.8414	Intermediate Similarity	NPC469680
0.8397	Intermediate Similarity	NPC185617
0.8394	Intermediate Similarity	NPC198014
0.8382	Intermediate Similarity	NPC253627
0.8369	Intermediate Similarity	NPC117609
0.8366	Intermediate Similarity	NPC476533
0.8345	Intermediate Similarity	NPC471152
0.8344	Intermediate Similarity	NPC46549
0.8344	Intermediate Similarity	NPC264229
0.8333	Intermediate Similarity	NPC471970
0.8333	Intermediate Similarity	NPC43353
0.8333	Intermediate Similarity	NPC283088
0.8333	Intermediate Similarity	NPC273798
0.8322	Intermediate Similarity	NPC145301
0.8322	Intermediate Similarity	NPC469375
0.8322	Intermediate Similarity	NPC144247
0.8322	Intermediate Similarity	NPC8493
0.8322	Intermediate Similarity	NPC477139
0.8322	Intermediate Similarity	NPC53896
0.8322	Intermediate Similarity	NPC4170
0.8322	Intermediate Similarity	NPC294679
0.8311	Intermediate Similarity	NPC477209
0.831	Intermediate Similarity	NPC85342
0.8301	Intermediate Similarity	NPC144283
0.8298	Intermediate Similarity	NPC146647
0.8298	Intermediate Similarity	NPC34414
0.8264	Intermediate Similarity	NPC50924
0.8264	Intermediate Similarity	NPC202225
0.8252	Intermediate Similarity	NPC58685
0.8227	Intermediate Similarity	NPC3009
0.8227	Intermediate Similarity	NPC48248
0.8224	Intermediate Similarity	NPC132810
0.8219	Intermediate Similarity	NPC147418
0.8212	Intermediate Similarity	NPC143685
0.8188	Intermediate Similarity	NPC477873
0.8188	Intermediate Similarity	NPC11250
0.8188	Intermediate Similarity	NPC85310
0.8188	Intermediate Similarity	NPC469447
0.8188	Intermediate Similarity	NPC469520
0.8182	Intermediate Similarity	NPC471851
0.8182	Intermediate Similarity	NPC70320
0.8169	Intermediate Similarity	NPC276238
0.8169	Intermediate Similarity	NPC99731
0.8156	Intermediate Similarity	NPC72667
0.8156	Intermediate Similarity	NPC78364
0.8156	Intermediate Similarity	NPC473787
0.8156	Intermediate Similarity	NPC176130
0.8156	Intermediate Similarity	NPC69424
0.8156	Intermediate Similarity	NPC84672
0.8151	Intermediate Similarity	NPC193358
0.8146	Intermediate Similarity	NPC75295
0.8146	Intermediate Similarity	NPC258856
0.8143	Intermediate Similarity	NPC137750
0.8143	Intermediate Similarity	NPC87985
0.8138	Intermediate Similarity	NPC161964
0.8138	Intermediate Similarity	NPC287604
0.8138	Intermediate Similarity	NPC472262
0.8129	Intermediate Similarity	NPC3744
0.8129	Intermediate Similarity	NPC137125
0.8129	Intermediate Similarity	NPC164912
0.8121	Intermediate Similarity	NPC92079
0.8117	Intermediate Similarity	NPC48949
0.8116	Intermediate Similarity	NPC154696
0.8112	Intermediate Similarity	NPC108129
0.8112	Intermediate Similarity	NPC55949
0.8099	Intermediate Similarity	NPC234175
0.8095	Intermediate Similarity	NPC475957
0.8095	Intermediate Similarity	NPC305060
0.8095	Intermediate Similarity	NPC53001
0.8092	Intermediate Similarity	NPC39361
0.8092	Intermediate Similarity	NPC63918
0.8089	Intermediate Similarity	NPC279605
0.8085	Intermediate Similarity	NPC3224
0.8085	Intermediate Similarity	NPC295202
0.8085	Intermediate Similarity	NPC254492
0.8085	Intermediate Similarity	NPC136342
0.8085	Intermediate Similarity	NPC49647
0.8085	Intermediate Similarity	NPC227741
0.8079	Intermediate Similarity	NPC309169
0.8079	Intermediate Similarity	NPC196941
0.8079	Intermediate Similarity	NPC53520
0.8079	Intermediate Similarity	NPC79627
0.8071	Intermediate Similarity	NPC234890
0.8071	Intermediate Similarity	NPC199273
0.8071	Intermediate Similarity	NPC15127
0.8071	Intermediate Similarity	NPC181334
0.8071	Intermediate Similarity	NPC74507
0.8069	Intermediate Similarity	NPC115458
0.8069	Intermediate Similarity	NPC78307
0.8069	Intermediate Similarity	NPC314048
0.8069	Intermediate Similarity	NPC52407
0.8067	Intermediate Similarity	NPC11314
0.8065	Intermediate Similarity	NPC35
0.8065	Intermediate Similarity	NPC118427
0.8065	Intermediate Similarity	NPC75377
0.8056	Intermediate Similarity	NPC72669
0.8056	Intermediate Similarity	NPC41847
0.8056	Intermediate Similarity	NPC17083
0.8056	Intermediate Similarity	NPC474517
0.8054	Intermediate Similarity	NPC203063
0.8052	Intermediate Similarity	NPC237441
0.8052	Intermediate Similarity	NPC142654
0.805	Intermediate Similarity	NPC141574
0.8043	Intermediate Similarity	NPC32322
0.8043	Intermediate Similarity	NPC259703
0.8042	Intermediate Similarity	NPC303910
0.8042	Intermediate Similarity	NPC25736
0.8042	Intermediate Similarity	NPC171460
0.8041	Intermediate Similarity	NPC87723
0.8039	Intermediate Similarity	NPC476821
0.8039	Intermediate Similarity	NPC52692
0.8027	Intermediate Similarity	NPC472308
0.8027	Intermediate Similarity	NPC315275
0.8027	Intermediate Similarity	NPC86524
0.8026	Intermediate Similarity	NPC73416
0.8026	Intermediate Similarity	NPC160777
0.8015	Intermediate Similarity	NPC16030
0.8014	Intermediate Similarity	NPC293454
0.8014	Intermediate Similarity	NPC131799
0.8	Intermediate Similarity	NPC91019
0.8	Intermediate Similarity	NPC472904
0.8	Intermediate Similarity	NPC471187
0.8	Intermediate Similarity	NPC375356
0.8	Intermediate Similarity	NPC187843
0.8	Intermediate Similarity	NPC106519
0.8	Intermediate Similarity	NPC280295
0.7987	Intermediate Similarity	NPC472903
0.7986	Intermediate Similarity	NPC136588
0.7986	Intermediate Similarity	NPC199253
0.7974	Intermediate Similarity	NPC477208
0.7973	Intermediate Similarity	NPC290030
0.7972	Intermediate Similarity	NPC282923
0.7972	Intermediate Similarity	NPC96024
0.7962	Intermediate Similarity	NPC474000
0.7962	Intermediate Similarity	NPC305710
0.7962	Intermediate Similarity	NPC475770
0.7961	Intermediate Similarity	NPC477913
0.7961	Intermediate Similarity	NPC300603

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 NPC199936 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	324
0.1-0.2	927
0.2-0.3	1498
0.3-0.4	2802
0.4-0.5	2179
0.5-0.6	1005
0.6-0.7	387
0.7-0.8	26
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8639	High Similarity	NPD7422	Clinical (unspecified phase)
0.8243	Intermediate Similarity	NPD8166	Discontinued
0.7887	Intermediate Similarity	NPD1470	Approved
0.7857	Intermediate Similarity	NPD1201	Approved
0.7778	Intermediate Similarity	NPD3300	Phase 2
0.7714	Intermediate Similarity	NPD3019	Approved
0.7714	Intermediate Similarity	NPD2932	Approved
0.7667	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7635	Intermediate Similarity	NPD943	Approved
0.7616	Intermediate Similarity	NPD5406	Approved
0.7616	Intermediate Similarity	NPD5404	Approved
0.7616	Intermediate Similarity	NPD5405	Approved
0.7616	Intermediate Similarity	NPD5408	Approved
0.7613	Intermediate Similarity	NPD7390	Discontinued
0.7572	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7554	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD7473	Discontinued
0.7434	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD7003	Approved
0.7407	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD7458	Discontinued
0.7333	Intermediate Similarity	NPD6663	Approved
0.732	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD6232	Discontinued
0.7297	Intermediate Similarity	NPD5736	Approved
0.7292	Intermediate Similarity	NPD3023	Approved
0.7292	Intermediate Similarity	NPD3026	Approved
0.7273	Intermediate Similarity	NPD3024	Approved
0.7273	Intermediate Similarity	NPD3025	Approved
0.7257	Intermediate Similarity	NPD8150	Discontinued
0.7174	Intermediate Similarity	NPD3022	Approved
0.7174	Intermediate Similarity	NPD3021	Approved
0.7161	Intermediate Similarity	NPD2935	Discontinued
0.7153	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6959	Discontinued
0.7134	Intermediate Similarity	NPD1934	Approved
0.7123	Intermediate Similarity	NPD3092	Approved
0.7118	Intermediate Similarity	NPD6166	Phase 2
0.7118	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD2346	Discontinued
0.7097	Intermediate Similarity	NPD2799	Discontinued
0.7091	Intermediate Similarity	NPD2801	Approved
0.7083	Intermediate Similarity	NPD3091	Approved
0.7067	Intermediate Similarity	NPD9494	Approved
0.7048	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD3094	Phase 2
0.7047	Intermediate Similarity	NPD1164	Approved
0.7029	Intermediate Similarity	NPD5028	Approved
0.7029	Intermediate Similarity	NPD4954	Approved
0.7029	Intermediate Similarity	NPD5026	Approved
0.7029	Intermediate Similarity	NPD5034	Approved
0.7029	Intermediate Similarity	NPD4955	Approved
0.7029	Intermediate Similarity	NPD36	Approved
0.7012	Intermediate Similarity	NPD7028	Phase 2
0.7006	Intermediate Similarity	NPD3882	Suspended
0.6989	Remote Similarity	NPD8312	Approved
0.6989	Remote Similarity	NPD8313	Approved
0.6988	Remote Similarity	NPD7819	Suspended
0.6986	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD6273	Approved
0.6971	Remote Similarity	NPD5030	Phase 2
0.6957	Remote Similarity	NPD1511	Approved
0.6954	Remote Similarity	NPD7074	Phase 3
0.6951	Remote Similarity	NPD3226	Approved
0.6948	Remote Similarity	NPD3620	Phase 2
0.6948	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5951	Approved
0.6909	Remote Similarity	NPD4380	Phase 2
0.6897	Remote Similarity	NPD7054	Approved
0.6887	Remote Similarity	NPD2798	Approved
0.6882	Remote Similarity	NPD5494	Approved
0.6875	Remote Similarity	NPD5029	Approved
0.6875	Remote Similarity	NPD5031	Approved
0.6875	Remote Similarity	NPD5027	Approved
0.6872	Remote Similarity	NPD5038	Approved
0.6872	Remote Similarity	NPD5037	Approved
0.6871	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD3095	Discontinued
0.6871	Remote Similarity	NPD1512	Approved
0.6859	Remote Similarity	NPD6651	Approved
0.6857	Remote Similarity	NPD7472	Approved
0.6848	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD3764	Approved
0.6816	Remote Similarity	NPD5036	Approved
0.6813	Remote Similarity	NPD5968	Phase 3
0.6813	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.681	Remote Similarity	NPD2533	Approved
0.681	Remote Similarity	NPD2534	Approved
0.681	Remote Similarity	NPD2532	Approved
0.681	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD7768	Phase 2
0.68	Remote Similarity	NPD5844	Phase 1
0.68	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD7635	Approved
0.678	Remote Similarity	NPD7251	Discontinued
0.6772	Remote Similarity	NPD1510	Phase 2
0.6765	Remote Similarity	NPD7075	Discontinued
0.6761	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD4059	Approved
0.6755	Remote Similarity	NPD1283	Approved
0.6753	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.675	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD8127	Discontinued
0.6743	Remote Similarity	NPD7228	Approved
0.6743	Remote Similarity	NPD3818	Discontinued
0.6738	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD4060	Phase 1
0.6725	Remote Similarity	NPD6234	Discontinued
0.6723	Remote Similarity	NPD6797	Phase 2
0.6722	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.671	Remote Similarity	NPD2313	Discontinued
0.6708	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6708	Remote Similarity	NPD2800	Approved
0.6707	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6704	Remote Similarity	NPD5035	Approved
0.6703	Remote Similarity	NPD6836	Approved
0.6689	Remote Similarity	NPD1651	Approved
0.6688	Remote Similarity	NPD230	Phase 1
0.6687	Remote Similarity	NPD2344	Approved
0.6686	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD6559	Discontinued
0.6685	Remote Similarity	NPD8434	Phase 2
0.6667	Remote Similarity	NPD8032	Phase 2
0.6667	Remote Similarity	NPD2342	Discontinued
0.6667	Remote Similarity	NPD4628	Phase 3
0.6667	Remote Similarity	NPD3750	Approved
0.6667	Remote Similarity	NPD7411	Suspended
0.6648	Remote Similarity	NPD7808	Phase 3
0.6647	Remote Similarity	NPD3817	Phase 2
0.6646	Remote Similarity	NPD1607	Approved
0.6645	Remote Similarity	NPD7008	Discontinued
0.6644	Remote Similarity	NPD4626	Approved
0.6629	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD37	Approved
0.6626	Remote Similarity	NPD6190	Approved
0.6624	Remote Similarity	NPD1240	Approved
0.6623	Remote Similarity	NPD3972	Approved
0.6623	Remote Similarity	NPD4878	Approved
0.6623	Remote Similarity	NPD9269	Phase 2
0.661	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD6599	Discontinued
0.6599	Remote Similarity	NPD9493	Approved
0.6588	Remote Similarity	NPD1465	Phase 2
0.6585	Remote Similarity	NPD7236	Approved
0.6584	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6584	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6584	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6582	Remote Similarity	NPD447	Suspended
0.6579	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6564	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6564	Remote Similarity	NPD4110	Phase 3
0.6564	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD6534	Approved
0.6559	Remote Similarity	NPD6535	Approved
0.6556	Remote Similarity	NPD1281	Approved
0.6556	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD5032	Approved
0.6554	Remote Similarity	NPD7610	Discontinued
0.6548	Remote Similarity	NPD3455	Phase 2
0.6543	Remote Similarity	NPD1549	Phase 2
0.6543	Remote Similarity	NPD7699	Phase 2
0.6543	Remote Similarity	NPD7700	Phase 2
0.6536	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6536	Remote Similarity	NPD1876	Approved
0.6529	Remote Similarity	NPD6801	Discontinued
0.6524	Remote Similarity	NPD2309	Approved
0.6522	Remote Similarity	NPD6099	Approved
0.6522	Remote Similarity	NPD6100	Approved
0.6522	Remote Similarity	NPD3020	Approved
0.6519	Remote Similarity	NPD825	Approved
0.6519	Remote Similarity	NPD2979	Phase 3
0.6519	Remote Similarity	NPD826	Approved
0.6512	Remote Similarity	NPD4967	Phase 2
0.6512	Remote Similarity	NPD4966	Approved
0.6512	Remote Similarity	NPD4965	Approved
0.651	Remote Similarity	NPD8320	Phase 1
0.651	Remote Similarity	NPD8319	Approved
0.6505	Remote Similarity	NPD6213	Phase 3
0.6505	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD6212	Phase 3
0.6503	Remote Similarity	NPD74	Approved
0.6503	Remote Similarity	NPD9266	Approved
0.6492	Remote Similarity	NPD2491	Approved
0.6492	Remote Similarity	NPD6823	Phase 2
0.6491	Remote Similarity	NPD5760	Phase 2
0.6491	Remote Similarity	NPD5761	Phase 2
0.6489	Remote Similarity	NPD7282	Approved
0.6483	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD7266	Discontinued
0.6478	Remote Similarity	NPD6355	Discontinued
0.6478	Remote Similarity	NPD5735	Approved
0.6474	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD6779	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