NPASS Compound

Structure

NPC470035 OpenBabel07101719162D 34 38 0 0 1 0 0 0 0 0999 V2000 -0.0999 1.2412 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0981 -0.3660 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 -1.7321 1.0000 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 5.0981 1.3660 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 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 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 -2.5981 0.5000 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 -3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 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 -4.3301 -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 -1.7321 0.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.5981 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 1 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0981 -0.3660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0981 1.3660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4 28 1 0 0 0 0 6 34 1 0 0 0 0 7 8 1 0 0 0 0 7 25 1 0 0 0 0 8 26 1 0 0 0 0 9 11 1 0 0 0 0 9 25 1 0 0 0 0 10 12 1 0 0 0 0 10 27 1 0 0 0 0 11 28 1 0 0 0 0 12 29 1 0 0 0 0 13 17 2 0 0 0 0 13 20 1 0 0 0 0 14 18 2 0 0 0 0 14 21 1 0 0 0 0 15 19 1 0 0 0 0 15 22 1 0 0 0 0 16 23 1 0 0 0 0 16 26 1 0 0 0 0 17 18 1 0 0 0 0 17 19 1 0 0 0 0 18 27 1 0 0 0 0 19 30 2 0 0 0 0 20 21 2 0 0 0 0 20 31 1 0 0 0 0 21 32 1 0 0 0 0 22 27 1 0 0 0 0 22 28 1 0 0 0 0 23 25 1 1 0 0 0 23 29 1 0 0 0 0 24 26 1 0 0 0 0 24 33 2 0 0 0 0 24 34 1 0 0 0 0 25 1 1 6 0 0 0 26 2 1 6 0 0 0 27 3 1 6 0 0 0 28 29 1 6 0 0 0 29 5 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	468.29
Volume:	498.127
LogP:	4.114
LogD:	3.616
LogS:	-5.091
# Rotatable Bonds:	2
TPSA:	83.83
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.382
Synthetic Accessibility Score:	4.682
Fsp3:	0.724
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.076
MDCK Permeability:	2.006982685998082e-05
Pgp-inhibitor:	0.724
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.027
30% Bioavailability (F30%):	0.937

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.138
Plasma Protein Binding (PPB):	97.24540710449219%
Volume Distribution (VD):	0.273
Pgp-substrate:	5.975461959838867%

ADMET: Metabolism

CYP1A2-inhibitor:	0.042
CYP1A2-substrate:	0.858
CYP2C19-inhibitor:	0.05
CYP2C19-substrate:	0.804
CYP2C9-inhibitor:	0.169
CYP2C9-substrate:	0.433
CYP2D6-inhibitor:	0.502
CYP2D6-substrate:	0.427
CYP3A4-inhibitor:	0.734
CYP3A4-substrate:	0.626

ADMET: Excretion

Clearance (CL):	7.145
Half-life (T1/2):	0.314

ADMET: Toxicity

hERG Blockers:	0.086
Human Hepatotoxicity (H-HT):	0.281
Drug-inuced Liver Injury (DILI):	0.114
AMES Toxicity:	0.076
Rat Oral Acute Toxicity:	0.076
Maximum Recommended Daily Dose:	0.835
Skin Sensitization:	0.848
Carcinogencity:	0.117
Eye Corrosion:	0.003
Eye Irritation:	0.485
Respiratory Toxicity:	0.54

Download Data

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

Natural Product: NPC470035

Natural Product ID:	NPC470035
*Common Name:**	23-Nor-Blepharodol
IUPAC Name:	methyl (2R,4aS,6aR,6aR,14aS,14bR)-10,11-dihydroxy-2,4a,6a,6a,14a-pentamethyl-8-oxo-1,3,4,5,6,6b,7,13,14,14b-decahydropicene-2-carboxylate
Synonyms:	23-Nor-Blepharodol
Standard InCHIKey:	YJMMRSBOXDGBDW-ZVHYNVNXSA-N
Standard InCHI:	InChI=1S/C29H40O5/c1-25-7-8-26(2,24(33)34-6)16-23(25)29(5)12-10-27(3)18-14-21(32)20(31)13-17(18)19(30)15-22(27)28(29,4)11-9-25/h13-14,22-23,31-32H,7-12,15-16H2,1-6H3/t22?,23-,25-,26-,27+,28-,29+/m1/s1
SMILES:	COC(=O)[C@]1(C)CC[C@]2([C@@H](C1)[C@]1(C)CC[C@@]3(C([C@]1(CC2)C)CC(=O)c1c3cc(O)c(c1)O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1651340
PubChem CID:	53320826
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
NPO25224	Maytenus retusa	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21090801]
NPO25224	Maytenus retusa	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
Others	6

Activity Type	# Activity
Cell Line	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	Inhibition	=	44.0	%	PMID[487051]
NPT83	Cell Line	MCF7	Homo sapiens	Inhibition	=	0.0	%	PMID[487051]
NPT83	Cell Line	MCF7	Homo sapiens	Inhibition	=	4.0	%	PMID[487051]
NPT116	Cell Line	HL-60	Homo sapiens	Inhibition	=	65.0	%	PMID[487051]
NPT116	Cell Line	HL-60	Homo sapiens	Inhibition	=	64.0	%	PMID[487051]
NPT116	Cell Line	HL-60	Homo sapiens	Inhibition	=	35.0	%	PMID[487051]

☑ 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 NPC470035 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	338
0.1-0.2	1414
0.2-0.3	2838
0.3-0.4	6695
0.4-0.5	10343
0.5-0.6	8960
0.6-0.7	10045
0.7-0.8	1860
0.8-0.85	168
0.85-0.9	27
0.9-0.95	5
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9562	High Similarity	NPC184935
0.9496	High Similarity	NPC470038
0.9338	High Similarity	NPC49911
0.9197	High Similarity	NPC277559
0.9167	High Similarity	NPC470037
0.9051	High Similarity	NPC43353
0.8993	High Similarity	NPC471974
0.8993	High Similarity	NPC469680
0.8993	High Similarity	NPC469681
0.8958	High Similarity	NPC10842
0.8905	High Similarity	NPC476282
0.8819	High Similarity	NPC75295
0.8786	High Similarity	NPC471152
0.8768	High Similarity	NPC4170
0.8768	High Similarity	NPC111845
0.8759	High Similarity	NPC243305
0.8741	High Similarity	NPC477873
0.8741	High Similarity	NPC469447
0.8714	High Similarity	NPC7464
0.8707	High Similarity	NPC142654
0.869	High Similarity	NPC258856
0.8633	High Similarity	NPC138472
0.8621	High Similarity	NPC53520
0.8601	High Similarity	NPC471853
0.8592	High Similarity	NPC149773
0.8592	High Similarity	NPC245760
0.8592	High Similarity	NPC23667
0.8592	High Similarity	NPC46242
0.8592	High Similarity	NPC473479
0.8592	High Similarity	NPC165191
0.8592	High Similarity	NPC469857
0.8592	High Similarity	NPC51531
0.8592	High Similarity	NPC157284
0.8592	High Similarity	NPC473779
0.8592	High Similarity	NPC114333
0.8592	High Similarity	NPC5014
0.8592	High Similarity	NPC297797
0.8592	High Similarity	NPC42384
0.8592	High Similarity	NPC28592
0.8592	High Similarity	NPC289358
0.8592	High Similarity	NPC50615
0.8592	High Similarity	NPC477849
0.8592	High Similarity	NPC91887
0.8562	High Similarity	NPC8102
0.8562	High Similarity	NPC66894
0.8562	High Similarity	NPC185617
0.8552	High Similarity	NPC199936
0.854	High Similarity	NPC234175
0.8531	High Similarity	NPC294330
0.8511	High Similarity	NPC103082
0.8511	High Similarity	NPC153088
0.8506	High Similarity	NPC266365
0.8493	Intermediate Similarity	NPC8493
0.8493	Intermediate Similarity	NPC469375
0.8493	Intermediate Similarity	NPC144247
0.8493	Intermediate Similarity	NPC145301
0.8493	Intermediate Similarity	NPC294679
0.8483	Intermediate Similarity	NPC248068
0.8483	Intermediate Similarity	NPC469855
0.8483	Intermediate Similarity	NPC192597
0.8483	Intermediate Similarity	NPC169214
0.8483	Intermediate Similarity	NPC471972
0.8483	Intermediate Similarity	NPC176030
0.8483	Intermediate Similarity	NPC141817
0.8483	Intermediate Similarity	NPC30846
0.8483	Intermediate Similarity	NPC471971
0.8483	Intermediate Similarity	NPC229218
0.8472	Intermediate Similarity	NPC476534
0.8472	Intermediate Similarity	NPC473527
0.8467	Intermediate Similarity	NPC124842
0.8462	Intermediate Similarity	NPC230811
0.844	Intermediate Similarity	NPC293454
0.84	Intermediate Similarity	NPC473680
0.84	Intermediate Similarity	NPC475311
0.84	Intermediate Similarity	NPC473579
0.84	Intermediate Similarity	NPC475454
0.8389	Intermediate Similarity	NPC46549
0.8389	Intermediate Similarity	NPC264229
0.8378	Intermediate Similarity	NPC273798
0.8378	Intermediate Similarity	NPC471970
0.8369	Intermediate Similarity	NPC475346
0.8369	Intermediate Similarity	NPC18982
0.8369	Intermediate Similarity	NPC475627
0.8369	Intermediate Similarity	NPC475457
0.8367	Intermediate Similarity	NPC196941
0.8367	Intermediate Similarity	NPC469856
0.8367	Intermediate Similarity	NPC469854
0.8367	Intermediate Similarity	NPC309169
0.8355	Intermediate Similarity	NPC62051
0.8345	Intermediate Similarity	NPC304110
0.8345	Intermediate Similarity	NPC27518
0.8333	Intermediate Similarity	NPC69424
0.8333	Intermediate Similarity	NPC78364
0.8333	Intermediate Similarity	NPC182249
0.8333	Intermediate Similarity	NPC84672
0.8333	Intermediate Similarity	NPC176130
0.8333	Intermediate Similarity	NPC327962
0.8322	Intermediate Similarity	NPC52692
0.831	Intermediate Similarity	NPC202225
0.8299	Intermediate Similarity	NPC25491
0.8291	Intermediate Similarity	NPC200726
0.8286	Intermediate Similarity	NPC108129
0.8278	Intermediate Similarity	NPC118033
0.8276	Intermediate Similarity	NPC155192
0.8276	Intermediate Similarity	NPC271494
0.8276	Intermediate Similarity	NPC473591
0.8267	Intermediate Similarity	NPC132810
0.8252	Intermediate Similarity	NPC173569
0.8252	Intermediate Similarity	NPC477874
0.8248	Intermediate Similarity	NPC15127
0.8247	Intermediate Similarity	NPC471968
0.8239	Intermediate Similarity	NPC177362
0.8239	Intermediate Similarity	NPC294226
0.8227	Intermediate Similarity	NPC18798
0.8227	Intermediate Similarity	NPC471851
0.8227	Intermediate Similarity	NPC291001
0.8224	Intermediate Similarity	NPC221249
0.8224	Intermediate Similarity	NPC475579
0.8224	Intermediate Similarity	NPC473773
0.8219	Intermediate Similarity	NPC172311
0.8219	Intermediate Similarity	NPC473612
0.8214	Intermediate Similarity	NPC303910
0.8212	Intermediate Similarity	NPC237441
0.8201	Intermediate Similarity	NPC324209
0.8201	Intermediate Similarity	NPC72667
0.82	Intermediate Similarity	NPC477483
0.82	Intermediate Similarity	NPC325032
0.8194	Intermediate Similarity	NPC249817
0.8187	Intermediate Similarity	NPC266545
0.8187	Intermediate Similarity	NPC202428
0.8182	Intermediate Similarity	NPC472807
0.817	Intermediate Similarity	NPC105942
0.817	Intermediate Similarity	NPC205392
0.8163	Intermediate Similarity	NPC35212
0.8146	Intermediate Similarity	NPC279442
0.8143	Intermediate Similarity	NPC229894
0.8138	Intermediate Similarity	NPC475482
0.8138	Intermediate Similarity	NPC264022
0.8138	Intermediate Similarity	NPC198621
0.8138	Intermediate Similarity	NPC475957
0.8138	Intermediate Similarity	NPC22676
0.8138	Intermediate Similarity	NPC216940
0.8137	Intermediate Similarity	NPC472803
0.8133	Intermediate Similarity	NPC474991
0.8129	Intermediate Similarity	NPC254492
0.8125	Intermediate Similarity	NPC258502
0.8125	Intermediate Similarity	NPC477596
0.8121	Intermediate Similarity	NPC126707
0.8117	Intermediate Similarity	NPC305710
0.8112	Intermediate Similarity	NPC477139
0.8112	Intermediate Similarity	NPC474715
0.8112	Intermediate Similarity	NPC78307
0.8108	Intermediate Similarity	NPC310621
0.8108	Intermediate Similarity	NPC252133
0.8102	Intermediate Similarity	NPC91478
0.8085	Intermediate Similarity	NPC171460
0.8085	Intermediate Similarity	NPC276238
0.8085	Intermediate Similarity	NPC117899
0.8082	Intermediate Similarity	NPC61398
0.8082	Intermediate Similarity	NPC234548
0.8082	Intermediate Similarity	NPC248287
0.8082	Intermediate Similarity	NPC416
0.8079	Intermediate Similarity	NPC470757
0.8079	Intermediate Similarity	NPC5568
0.8074	Intermediate Similarity	NPC42657
0.8067	Intermediate Similarity	NPC84786
0.8058	Intermediate Similarity	NPC137416
0.8056	Intermediate Similarity	NPC477594
0.8056	Intermediate Similarity	NPC204582
0.8054	Intermediate Similarity	NPC100242
0.8041	Intermediate Similarity	NPC2681
0.8041	Intermediate Similarity	NPC272907
0.8029	Intermediate Similarity	NPC120545
0.8028	Intermediate Similarity	NPC117609
0.8014	Intermediate Similarity	NPC147418
0.8014	Intermediate Similarity	NPC193203
0.8014	Intermediate Similarity	NPC3009
0.8014	Intermediate Similarity	NPC477592
0.8013	Intermediate Similarity	NPC191899
0.8013	Intermediate Similarity	NPC58752
0.8013	Intermediate Similarity	NPC246229
0.8013	Intermediate Similarity	NPC477208
0.8	Intermediate Similarity	NPC15837
0.8	Intermediate Similarity	NPC89504
0.8	Intermediate Similarity	NPC307205
0.8	Intermediate Similarity	NPC95485
0.8	Intermediate Similarity	NPC72918
0.8	Intermediate Similarity	NPC88065
0.7987	Intermediate Similarity	NPC477209
0.7987	Intermediate Similarity	NPC235557
0.7986	Intermediate Similarity	NPC239855
0.7986	Intermediate Similarity	NPC49742
0.7986	Intermediate Similarity	NPC199273
0.7974	Intermediate Similarity	NPC303989
0.7974	Intermediate Similarity	NPC261322
0.7973	Intermediate Similarity	NPC3218
0.7973	Intermediate Similarity	NPC290664
0.7961	Intermediate Similarity	NPC127046
0.7961	Intermediate Similarity	NPC17042
0.7961	Intermediate Similarity	NPC155910

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 NPC470035 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	290
0.1-0.2	902
0.2-0.3	1532
0.3-0.4	2728
0.4-0.5	2222
0.5-0.6	1067
0.6-0.7	381
0.7-0.8	27
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8936	High Similarity	NPD8166	Discontinued
0.7974	Intermediate Similarity	NPD7458	Discontinued
0.7919	Intermediate Similarity	NPD7003	Approved
0.7829	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7754	Intermediate Similarity	NPD3019	Approved
0.7724	Intermediate Similarity	NPD6663	Approved
0.7692	Intermediate Similarity	NPD5736	Approved
0.7626	Intermediate Similarity	NPD2932	Approved
0.7548	Intermediate Similarity	NPD6273	Approved
0.7533	Intermediate Similarity	NPD5408	Approved
0.7533	Intermediate Similarity	NPD5404	Approved
0.7533	Intermediate Similarity	NPD5405	Approved
0.7533	Intermediate Similarity	NPD5406	Approved
0.7532	Intermediate Similarity	NPD7390	Discontinued
0.7515	Intermediate Similarity	NPD7473	Discontinued
0.75	Intermediate Similarity	NPD230	Phase 1
0.75	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7465	Intermediate Similarity	NPD9269	Phase 2
0.7432	Intermediate Similarity	NPD943	Approved
0.7431	Intermediate Similarity	NPD1470	Approved
0.7415	Intermediate Similarity	NPD3764	Approved
0.7346	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD4628	Phase 3
0.7333	Intermediate Similarity	NPD6232	Discontinued
0.7324	Intermediate Similarity	NPD3023	Approved
0.7324	Intermediate Similarity	NPD3026	Approved
0.7319	Intermediate Similarity	NPD5951	Approved
0.7305	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD3024	Approved
0.7305	Intermediate Similarity	NPD3025	Approved
0.729	Intermediate Similarity	NPD6190	Approved
0.7273	Intermediate Similarity	NPD1201	Approved
0.7237	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD1465	Phase 2
0.7211	Intermediate Similarity	NPD9494	Approved
0.7206	Intermediate Similarity	NPD3022	Approved
0.7206	Intermediate Similarity	NPD3021	Approved
0.7183	Intermediate Similarity	NPD9268	Approved
0.7169	Intermediate Similarity	NPD8127	Discontinued
0.7135	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD3300	Phase 2
0.7133	Intermediate Similarity	NPD8032	Phase 2
0.7133	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD1283	Approved
0.7118	Intermediate Similarity	NPD5844	Phase 1
0.7114	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD7008	Discontinued
0.7103	Intermediate Similarity	NPD3972	Approved
0.7089	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD8150	Discontinued
0.7086	Intermediate Similarity	NPD3620	Phase 2
0.7078	Intermediate Similarity	NPD2935	Discontinued
0.7073	Intermediate Similarity	NPD8438	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7228	Approved
0.7055	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD6234	Discontinued
0.7037	Intermediate Similarity	NPD7028	Phase 2
0.7034	Intermediate Similarity	NPD3092	Approved
0.7032	Intermediate Similarity	NPD2346	Discontinued
0.7025	Intermediate Similarity	NPD7236	Approved
0.7013	Intermediate Similarity	NPD2799	Discontinued
0.7013	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD7819	Suspended
0.7012	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD8313	Approved
0.7011	Intermediate Similarity	NPD8312	Approved
0.7007	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD9545	Approved
0.6993	Remote Similarity	NPD3091	Approved
0.6987	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD3226	Approved
0.6975	Remote Similarity	NPD3455	Phase 2
0.6972	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD6959	Discontinued
0.6959	Remote Similarity	NPD3094	Phase 2
0.6957	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD37	Approved
0.6934	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7266	Discontinued
0.6918	Remote Similarity	NPD1281	Approved
0.6914	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD2801	Approved
0.6908	Remote Similarity	NPD7961	Discontinued
0.6899	Remote Similarity	NPD4110	Phase 3
0.6899	Remote Similarity	NPD3750	Approved
0.6899	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD7685	Pre-registration
0.689	Remote Similarity	NPD6873	Phase 2
0.6887	Remote Similarity	NPD7095	Approved
0.6863	Remote Similarity	NPD825	Approved
0.6863	Remote Similarity	NPD826	Approved
0.6848	Remote Similarity	NPD1934	Approved
0.6846	Remote Similarity	NPD1164	Approved
0.6842	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD6166	Phase 2
0.6832	Remote Similarity	NPD2534	Approved
0.6832	Remote Similarity	NPD2532	Approved
0.6832	Remote Similarity	NPD2533	Approved
0.6831	Remote Similarity	NPD2629	Approved
0.6826	Remote Similarity	NPD3882	Suspended
0.6826	Remote Similarity	NPD4965	Approved
0.6826	Remote Similarity	NPD4966	Approved
0.6826	Remote Similarity	NPD4967	Phase 2
0.681	Remote Similarity	NPD7239	Suspended
0.6806	Remote Similarity	NPD7610	Discontinued
0.68	Remote Similarity	NPD258	Approved
0.68	Remote Similarity	NPD257	Approved
0.6786	Remote Similarity	NPD7075	Discontinued
0.6782	Remote Similarity	NPD7074	Phase 3
0.6781	Remote Similarity	NPD4626	Approved
0.6781	Remote Similarity	NPD4059	Approved
0.6781	Remote Similarity	NPD3095	Discontinued
0.6779	Remote Similarity	NPD1876	Approved
0.677	Remote Similarity	NPD1511	Approved
0.6757	Remote Similarity	NPD4878	Approved
0.6753	Remote Similarity	NPD2979	Phase 3
0.6753	Remote Similarity	NPD4060	Phase 1
0.6753	Remote Similarity	NPD4140	Approved
0.6752	Remote Similarity	NPD6099	Approved
0.6752	Remote Similarity	NPD6100	Approved
0.675	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD6599	Discontinued
0.6726	Remote Similarity	NPD7768	Phase 2
0.6724	Remote Similarity	NPD7054	Approved
0.6712	Remote Similarity	NPD1651	Approved
0.6707	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6704	Remote Similarity	NPD8434	Phase 2
0.6689	Remote Similarity	NPD2798	Approved
0.6688	Remote Similarity	NPD259	Phase 1
0.6687	Remote Similarity	NPD7411	Suspended
0.6687	Remote Similarity	NPD1512	Approved
0.6686	Remote Similarity	NPD3749	Approved
0.6686	Remote Similarity	NPD7472	Approved
0.6667	Remote Similarity	NPD7177	Discontinued
0.6667	Remote Similarity	NPD3817	Phase 2
0.6667	Remote Similarity	NPD3818	Discontinued
0.6667	Remote Similarity	NPD5978	Approved
0.6667	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5977	Approved
0.6649	Remote Similarity	NPD8151	Discontinued
0.6646	Remote Similarity	NPD2438	Suspended
0.6644	Remote Similarity	NPD1608	Approved
0.6642	Remote Similarity	NPD1930	Approved
0.6642	Remote Similarity	NPD1929	Approved
0.6642	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD4380	Phase 2
0.6626	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6624	Remote Similarity	NPD7097	Phase 1
0.6623	Remote Similarity	NPD3268	Approved
0.6623	Remote Similarity	NPD2313	Discontinued
0.6621	Remote Similarity	NPD9493	Approved
0.6614	Remote Similarity	NPD8320	Phase 1
0.6614	Remote Similarity	NPD8319	Approved
0.661	Remote Similarity	NPD7240	Approved
0.661	Remote Similarity	NPD7251	Discontinued
0.6608	Remote Similarity	NPD5494	Approved
0.6604	Remote Similarity	NPD2344	Approved
0.6603	Remote Similarity	NPD447	Suspended
0.6603	Remote Similarity	NPD6355	Discontinued
0.6603	Remote Similarity	NPD555	Phase 2
0.66	Remote Similarity	NPD1755	Approved
0.6592	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD6385	Approved
0.6587	Remote Similarity	NPD6386	Approved
0.6582	Remote Similarity	NPD3748	Approved
0.6582	Remote Similarity	NPD1510	Phase 2
0.6575	Remote Similarity	NPD5536	Phase 2
0.6573	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.657	Remote Similarity	NPD7199	Phase 2
0.6561	Remote Similarity	NPD1607	Approved
0.6561	Remote Similarity	NPD6651	Approved
0.6561	Remote Similarity	NPD7435	Discontinued
0.6554	Remote Similarity	NPD6797	Phase 2
0.6549	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6548	Remote Similarity	NPD6801	Discontinued
0.6544	Remote Similarity	NPD3020	Approved
0.6544	Remote Similarity	NPD2066	Phase 3
0.6543	Remote Similarity	NPD2354	Approved
0.6541	Remote Similarity	NPD2531	Phase 2
0.6538	Remote Similarity	NPD1240	Approved
0.6536	Remote Similarity	NPD9569	Approved
0.6524	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6516	Remote Similarity	NPD6798	Discontinued
0.6513	Remote Similarity	NPD2797	Approved
0.6503	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.65	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6497	Remote Similarity	NPD275	Approved
0.6497	Remote Similarity	NPD5735	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