NPASS Compound

Structure

NPC186033 OpenBabel07101718322D 33 37 0 0 1 0 0 0 0 0999 V2000 -4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 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 -0.8660 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -3.5000 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 -2.5981 -3.5000 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 3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 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 -4.3301 -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 -1.7321 -3.0000 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 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 1 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 -2.5981 -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 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -3.5000 0.0000 C 0 0 0 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 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 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 15 1 0 0 0 0 3 16 1 0 0 0 0 4 16 1 0 0 0 0 5 17 1 0 0 0 0 6 18 1 0 0 0 0 7 19 1 0 0 0 0 8 9 2 0 0 0 0 8 17 1 0 0 0 0 9 20 1 0 0 0 0 10 18 1 0 0 0 0 10 22 2 0 0 0 0 11 19 2 0 0 0 0 11 23 1 0 0 0 0 12 21 1 0 0 0 0 12 27 1 0 0 0 0 13 25 2 0 0 0 0 13 26 1 0 0 0 0 14 24 1 0 0 0 0 14 30 1 0 0 0 0 15 20 1 0 0 0 0 17 28 2 0 0 0 0 18 26 2 0 0 0 0 19 29 1 0 0 0 0 20 23 2 0 0 0 0 21 16 1 1 0 0 0 21 22 1 0 0 0 0 22 25 1 0 0 0 0 23 28 1 0 0 0 0 24 28 1 0 0 0 0 24 29 2 0 0 0 0 25 30 1 0 0 0 0 26 31 1 0 0 0 0 27 30 1 6 0 0 0 27 33 1 0 0 0 0 29 33 1 0 0 0 0 30 32 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	444.27
Volume:	489.933
LogP:	7.24
LogD:	5.047
LogS:	-7.08
# Rotatable Bonds:	2
TPSA:	49.69
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.451
Synthetic Accessibility Score:	4.338
Fsp3:	0.467
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.533
MDCK Permeability:	1.1947635357500985e-05
Pgp-inhibitor:	0.924
Pgp-substrate:	0.186
Human Intestinal Absorption (HIA):	0.096
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.177
Plasma Protein Binding (PPB):	99.79764556884766%
Volume Distribution (VD):	1.411
Pgp-substrate:	1.4320626258850098%

ADMET: Metabolism

CYP1A2-inhibitor:	0.118
CYP1A2-substrate:	0.947
CYP2C19-inhibitor:	0.73
CYP2C19-substrate:	0.853
CYP2C9-inhibitor:	0.455
CYP2C9-substrate:	0.961
CYP2D6-inhibitor:	0.272
CYP2D6-substrate:	0.931
CYP3A4-inhibitor:	0.335
CYP3A4-substrate:	0.911

ADMET: Excretion

Clearance (CL):	5.975
Half-life (T1/2):	0.032

ADMET: Toxicity

hERG Blockers:	0.428
Human Hepatotoxicity (H-HT):	0.082
Drug-inuced Liver Injury (DILI):	0.689
AMES Toxicity:	0.235
Rat Oral Acute Toxicity:	0.851
Maximum Recommended Daily Dose:	0.977
Skin Sensitization:	0.733
Carcinogencity:	0.306
Eye Corrosion:	0.003
Eye Irritation:	0.441
Respiratory Toxicity:	0.732

Download Data

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

Natural Product: NPC186033

Natural Product ID:	NPC186033
*Common Name:**	Dicadalenol
IUPAC Name:	n.a.
Synonyms:	dicadalenol
Standard InCHIKey:	DDVIVMMKNAZNJE-FXBCZQQTSA-N
Standard InCHI:	InChI=1S/C30H36O3/c1-15(2)20-9-8-17(5)28-23(20)11-19(7)29-24(28)14-30(32)25-13-26(31)18(6)10-22(25)21(16(3)4)12-27(30)33-29/h8-11,13,15-16,21,27,31-32H,12,14H2,1-7H3/t21-,27+,30+/m0/s1
SMILES:	CC([C@@H]1C[C@H]2Oc3c(C)cc4c(c3C[C@]2(c2c1cc(C)c(c2)O)O)c(C)ccc4C(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL518495
PubChem CID:	10252903
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0001612] Isoflavans

*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
NPO25769	Heterotheca inuloides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11473412]
NPO25769	Heterotheca inuloides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26566007]
NPO25769	Heterotheca inuloides	Species	Asteraceae	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
ED50	1
Others	4

Activity Type	# Activity
Organism	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT32	Organism	Mus musculus	Mus musculus	ED50	=	0.11	mg	PMID[524795]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	17.08	%	PMID[524795]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	29.45	%	PMID[524795]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	57.06	%	PMID[524795]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	70.15	%	PMID[524795]

☑ 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 NPC186033 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	454
0.1-0.2	1600
0.2-0.3	3744
0.3-0.4	10441
0.4-0.5	8339
0.5-0.6	3978
0.6-0.7	8935
0.7-0.8	4391
0.8-0.85	715
0.85-0.9	96
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8889	High Similarity	NPC274454
0.8889	High Similarity	NPC215678
0.8828	High Similarity	NPC153182
0.8828	High Similarity	NPC174251
0.8784	High Similarity	NPC325860
0.8776	High Similarity	NPC158784
0.8759	High Similarity	NPC233980
0.8741	High Similarity	NPC470724
0.8716	High Similarity	NPC2745
0.8716	High Similarity	NPC302915
0.8699	High Similarity	NPC474397
0.8671	High Similarity	NPC265075
0.8667	High Similarity	NPC188578
0.8667	High Similarity	NPC80918
0.8658	High Similarity	NPC157783
0.8658	High Similarity	NPC160196
0.8652	High Similarity	NPC472800
0.8649	High Similarity	NPC195561
0.8649	High Similarity	NPC477612
0.8643	High Similarity	NPC71372
0.8643	High Similarity	NPC184269
0.8643	High Similarity	NPC141023
0.8639	High Similarity	NPC212142
0.8633	High Similarity	NPC303144
0.8633	High Similarity	NPC27578
0.8633	High Similarity	NPC289624
0.8633	High Similarity	NPC189482
0.8633	High Similarity	NPC228843
0.8621	High Similarity	NPC473845
0.8621	High Similarity	NPC475492
0.8621	High Similarity	NPC473108
0.8613	High Similarity	NPC471064
0.8581	High Similarity	NPC321657
0.8581	High Similarity	NPC44452
0.8581	High Similarity	NPC318373
0.8581	High Similarity	NPC211561
0.8571	High Similarity	NPC58190
0.8571	High Similarity	NPC70409
0.8571	High Similarity	NPC170103
0.8571	High Similarity	NPC204770
0.8571	High Similarity	NPC294558
0.8571	High Similarity	NPC211352
0.8571	High Similarity	NPC262911
0.8571	High Similarity	NPC18185
0.8571	High Similarity	NPC469610
0.8571	High Similarity	NPC263940
0.8571	High Similarity	NPC82917
0.8571	High Similarity	NPC108811
0.8571	High Similarity	NPC236202
0.8571	High Similarity	NPC202742
0.8562	High Similarity	NPC469557
0.8561	High Similarity	NPC160623
0.8561	High Similarity	NPC153019
0.8542	High Similarity	NPC277331
0.8542	High Similarity	NPC100482
0.854	High Similarity	NPC471077
0.854	High Similarity	NPC186889
0.8533	High Similarity	NPC474442
0.8533	High Similarity	NPC476391
0.8531	High Similarity	NPC32630
0.8529	High Similarity	NPC470726
0.8523	High Similarity	NPC118000
0.8523	High Similarity	NPC205501
0.8523	High Similarity	NPC162976
0.8521	High Similarity	NPC472648
0.8521	High Similarity	NPC471522
0.8521	High Similarity	NPC472649
0.8521	High Similarity	NPC68292
0.8521	High Similarity	NPC133463
0.8521	High Similarity	NPC472647
0.8521	High Similarity	NPC206525
0.8521	High Similarity	NPC170328
0.8521	High Similarity	NPC126101
0.8521	High Similarity	NPC191462
0.8514	High Similarity	NPC473876
0.8514	High Similarity	NPC227516
0.8514	High Similarity	NPC20757
0.8511	High Similarity	NPC471942
0.8511	High Similarity	NPC49603
0.8511	High Similarity	NPC311256
0.8511	High Similarity	NPC473107
0.8511	High Similarity	NPC187616
0.8511	High Similarity	NPC193026
0.8503	High Similarity	NPC96576
0.85	High Similarity	NPC469611
0.85	High Similarity	NPC73656
0.8493	Intermediate Similarity	NPC50250
0.8493	Intermediate Similarity	NPC469795
0.8489	Intermediate Similarity	NPC470727
0.8489	Intermediate Similarity	NPC196193
0.8483	Intermediate Similarity	NPC204347
0.8483	Intermediate Similarity	NPC475891
0.8483	Intermediate Similarity	NPC2613
0.8483	Intermediate Similarity	NPC59841
0.8483	Intermediate Similarity	NPC183709
0.8478	Intermediate Similarity	NPC47288
0.8472	Intermediate Similarity	NPC12668
0.8472	Intermediate Similarity	NPC221134
0.8472	Intermediate Similarity	NPC308768
0.8472	Intermediate Similarity	NPC273623
0.8462	Intermediate Similarity	NPC266006
0.8462	Intermediate Similarity	NPC71465
0.8462	Intermediate Similarity	NPC470307
0.8462	Intermediate Similarity	NPC470308
0.8462	Intermediate Similarity	NPC472646
0.8456	Intermediate Similarity	NPC476969
0.8456	Intermediate Similarity	NPC61685
0.8451	Intermediate Similarity	NPC258780
0.8451	Intermediate Similarity	NPC37410
0.8446	Intermediate Similarity	NPC262297
0.844	Intermediate Similarity	NPC92805
0.844	Intermediate Similarity	NPC227719
0.8435	Intermediate Similarity	NPC90645
0.8429	Intermediate Similarity	NPC282508
0.8429	Intermediate Similarity	NPC8899
0.8429	Intermediate Similarity	NPC472590
0.8425	Intermediate Similarity	NPC163508
0.8425	Intermediate Similarity	NPC469630
0.8425	Intermediate Similarity	NPC173203
0.8421	Intermediate Similarity	NPC157333
0.8417	Intermediate Similarity	NPC222108
0.8417	Intermediate Similarity	NPC96719
0.8417	Intermediate Similarity	NPC16577
0.8414	Intermediate Similarity	NPC178054
0.8414	Intermediate Similarity	NPC470372
0.8414	Intermediate Similarity	NPC71046
0.8411	Intermediate Similarity	NPC279406
0.8411	Intermediate Similarity	NPC226809
0.8403	Intermediate Similarity	NPC260842
0.8403	Intermediate Similarity	NPC220344
0.8403	Intermediate Similarity	NPC243996
0.8403	Intermediate Similarity	NPC243759
0.8403	Intermediate Similarity	NPC218131
0.8403	Intermediate Similarity	NPC260741
0.8403	Intermediate Similarity	NPC275061
0.8403	Intermediate Similarity	NPC475836
0.8403	Intermediate Similarity	NPC132804
0.8403	Intermediate Similarity	NPC105847
0.8403	Intermediate Similarity	NPC70682
0.84	Intermediate Similarity	NPC183380
0.8392	Intermediate Similarity	NPC327735
0.8392	Intermediate Similarity	NPC77861
0.8392	Intermediate Similarity	NPC177160
0.8392	Intermediate Similarity	NPC262585
0.8392	Intermediate Similarity	NPC10737
0.8392	Intermediate Similarity	NPC141717
0.8392	Intermediate Similarity	NPC209985
0.8392	Intermediate Similarity	NPC263367
0.8392	Intermediate Similarity	NPC234952
0.8392	Intermediate Similarity	NPC20829
0.8392	Intermediate Similarity	NPC18189
0.8392	Intermediate Similarity	NPC477939
0.8392	Intermediate Similarity	NPC156502
0.8392	Intermediate Similarity	NPC54743
0.8392	Intermediate Similarity	NPC29799
0.838	Intermediate Similarity	NPC124085
0.838	Intermediate Similarity	NPC478085
0.838	Intermediate Similarity	NPC117048
0.8378	Intermediate Similarity	NPC260397
0.8378	Intermediate Similarity	NPC14468
0.8378	Intermediate Similarity	NPC126291
0.8378	Intermediate Similarity	NPC471608
0.8369	Intermediate Similarity	NPC472798
0.8367	Intermediate Similarity	NPC15659
0.8367	Intermediate Similarity	NPC133251
0.8367	Intermediate Similarity	NPC164183
0.8367	Intermediate Similarity	NPC304894
0.8367	Intermediate Similarity	NPC151704
0.8358	Intermediate Similarity	NPC103916
0.8357	Intermediate Similarity	NPC143483
0.8357	Intermediate Similarity	NPC99795
0.8356	Intermediate Similarity	NPC175838
0.8355	Intermediate Similarity	NPC106669
0.8355	Intermediate Similarity	NPC200645
0.8355	Intermediate Similarity	NPC224161
0.8355	Intermediate Similarity	NPC475227
0.8345	Intermediate Similarity	NPC215300
0.8345	Intermediate Similarity	NPC38017
0.8345	Intermediate Similarity	NPC22317
0.8333	Intermediate Similarity	NPC266453
0.8333	Intermediate Similarity	NPC35550
0.8333	Intermediate Similarity	NPC22902
0.8333	Intermediate Similarity	NPC151656
0.8333	Intermediate Similarity	NPC56329
0.8333	Intermediate Similarity	NPC474687
0.8333	Intermediate Similarity	NPC200935
0.8333	Intermediate Similarity	NPC230919
0.8333	Intermediate Similarity	NPC242715
0.8322	Intermediate Similarity	NPC11727
0.8322	Intermediate Similarity	NPC151224
0.8322	Intermediate Similarity	NPC21776
0.8322	Intermediate Similarity	NPC93783
0.8322	Intermediate Similarity	NPC473413
0.8322	Intermediate Similarity	NPC125579
0.8322	Intermediate Similarity	NPC15109
0.8322	Intermediate Similarity	NPC16269
0.8311	Intermediate Similarity	NPC221318
0.8311	Intermediate Similarity	NPC271076
0.8311	Intermediate Similarity	NPC472457
0.8311	Intermediate Similarity	NPC286245

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 NPC186033 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	398
0.1-0.2	905
0.2-0.3	1603
0.3-0.4	2702
0.4-0.5	1725
0.5-0.6	985
0.6-0.7	658
0.7-0.8	165
0.8-0.85	9
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8417	Intermediate Similarity	NPD4625	Phase 3
0.8357	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8288	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.8288	Intermediate Similarity	NPD6674	Discontinued
0.8273	Intermediate Similarity	NPD2861	Phase 2
0.8214	Intermediate Similarity	NPD4908	Phase 1
0.8112	Intermediate Similarity	NPD4060	Phase 1
0.7986	Intermediate Similarity	NPD1613	Approved
0.7986	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7972	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7931	Intermediate Similarity	NPD5735	Approved
0.7929	Intermediate Similarity	NPD6696	Suspended
0.7857	Intermediate Similarity	NPD4749	Approved
0.7842	Intermediate Similarity	NPD1610	Phase 2
0.7832	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7794	Intermediate Similarity	NPD7340	Approved
0.7764	Intermediate Similarity	NPD6959	Discontinued
0.7762	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD3620	Phase 2
0.774	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD5327	Phase 3
0.773	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7724	Intermediate Similarity	NPD6812	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD8455	Phase 2
0.7721	Intermediate Similarity	NPD6671	Approved
0.7703	Intermediate Similarity	NPD7097	Phase 1
0.7697	Intermediate Similarity	NPD5844	Phase 1
0.7676	Intermediate Similarity	NPD8651	Approved
0.7667	Intermediate Similarity	NPD5763	Approved
0.7667	Intermediate Similarity	NPD5762	Approved
0.7662	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7662	Intermediate Similarity	NPD7446	Clinical (unspecified phase)
0.7655	Intermediate Similarity	NPD3027	Phase 3
0.7635	Intermediate Similarity	NPD6353	Approved
0.7616	Intermediate Similarity	NPD7037	Approved
0.7597	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD7041	Phase 2
0.7574	Intermediate Similarity	NPD8313	Approved
0.7574	Intermediate Similarity	NPD8312	Approved
0.7574	Intermediate Similarity	NPD1398	Phase 1
0.7548	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD7003	Approved
0.75	Intermediate Similarity	NPD5929	Approved
0.75	Intermediate Similarity	NPD7635	Approved
0.75	Intermediate Similarity	NPD4140	Approved
0.7483	Intermediate Similarity	NPD6100	Approved
0.7483	Intermediate Similarity	NPD6099	Approved
0.7468	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD4536	Approved
0.7467	Intermediate Similarity	NPD4538	Approved
0.7457	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD6584	Phase 3
0.7447	Intermediate Similarity	NPD4626	Approved
0.7445	Intermediate Similarity	NPD4869	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD1548	Phase 1
0.7425	Intermediate Similarity	NPD7228	Approved
0.7415	Intermediate Similarity	NPD7095	Approved
0.74	Intermediate Similarity	NPD4097	Suspended
0.7394	Intermediate Similarity	NPD3051	Approved
0.7394	Intermediate Similarity	NPD3787	Discontinued
0.7391	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7388	Intermediate Similarity	NPD2342	Discontinued
0.7383	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.7376	Intermediate Similarity	NPD5691	Approved
0.7368	Intermediate Similarity	NPD7310	Approved
0.7368	Intermediate Similarity	NPD7312	Approved
0.7368	Intermediate Similarity	NPD7311	Approved
0.7368	Intermediate Similarity	NPD7313	Approved
0.7365	Intermediate Similarity	NPD6798	Discontinued
0.7365	Intermediate Similarity	NPD7473	Discontinued
0.7355	Intermediate Similarity	NPD2677	Approved
0.7349	Intermediate Similarity	NPD2970	Approved
0.7349	Intermediate Similarity	NPD2969	Approved
0.7346	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7343	Intermediate Similarity	NPD3092	Approved
0.7343	Intermediate Similarity	NPD1611	Approved
0.7338	Intermediate Similarity	NPD7157	Approved
0.7333	Intermediate Similarity	NPD2684	Approved
0.7333	Intermediate Similarity	NPD6355	Discontinued
0.7329	Intermediate Similarity	NPD4624	Approved
0.7326	Intermediate Similarity	NPD7309	Approved
0.7325	Intermediate Similarity	NPD7447	Phase 1
0.7324	Intermediate Similarity	NPD6516	Phase 2
0.7324	Intermediate Similarity	NPD5846	Approved
0.7319	Intermediate Similarity	NPD5283	Phase 1
0.7317	Intermediate Similarity	NPD6234	Discontinued
0.731	Intermediate Similarity	NPD1283	Approved
0.7308	Intermediate Similarity	NPD5058	Phase 3
0.7305	Intermediate Similarity	NPD6166	Phase 2
0.7305	Intermediate Similarity	NPD2489	Approved
0.7305	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD27	Approved
0.7303	Intermediate Similarity	NPD5588	Approved
0.7303	Intermediate Similarity	NPD5960	Phase 3
0.7301	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD6232	Discontinued
0.7273	Intermediate Similarity	NPD4666	Phase 3
0.7267	Intermediate Similarity	NPD4577	Approved
0.7267	Intermediate Similarity	NPD4578	Approved
0.7261	Intermediate Similarity	NPD7213	Phase 3
0.7261	Intermediate Similarity	NPD7212	Phase 2
0.726	Intermediate Similarity	NPD3094	Phase 2
0.7256	Intermediate Similarity	NPD7831	Phase 2
0.7256	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD7833	Phase 2
0.7254	Intermediate Similarity	NPD1651	Approved
0.7248	Intermediate Similarity	NPD7294	Phase 1
0.7248	Intermediate Similarity	NPD7985	Registered
0.7246	Intermediate Similarity	NPD7843	Approved
0.7241	Intermediate Similarity	NPD6582	Phase 2
0.7241	Intermediate Similarity	NPD6583	Phase 3
0.7229	Intermediate Similarity	NPD8127	Discontinued
0.7222	Intermediate Similarity	NPD37	Approved
0.7222	Intermediate Similarity	NPD1091	Approved
0.7222	Intermediate Similarity	NPD1934	Approved
0.7219	Intermediate Similarity	NPD5124	Phase 1
0.7219	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD5709	Phase 3
0.7203	Intermediate Similarity	NPD5125	Phase 3
0.7203	Intermediate Similarity	NPD5126	Approved
0.72	Intermediate Similarity	NPD7906	Approved
0.7197	Intermediate Similarity	NPD6815	Approved
0.7195	Intermediate Similarity	NPD4966	Approved
0.7195	Intermediate Similarity	NPD7768	Phase 2
0.7195	Intermediate Similarity	NPD4965	Approved
0.7195	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD4967	Phase 2
0.719	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD7229	Phase 3
0.7183	Intermediate Similarity	NPD3091	Approved
0.7179	Intermediate Similarity	NPD4628	Phase 3
0.7179	Intermediate Similarity	NPD6331	Phase 2
0.7179	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD7466	Approved
0.7175	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD228	Approved
0.717	Intermediate Similarity	NPD6090	Discontinued
0.717	Intermediate Similarity	NPD6273	Approved
0.7152	Intermediate Similarity	NPD2979	Phase 3
0.7152	Intermediate Similarity	NPD2238	Phase 2
0.7151	Intermediate Similarity	NPD6559	Discontinued
0.7143	Intermediate Similarity	NPD4663	Approved
0.7143	Intermediate Similarity	NPD2438	Suspended
0.7143	Intermediate Similarity	NPD7458	Discontinued
0.7132	Intermediate Similarity	NPD290	Approved
0.7126	Intermediate Similarity	NPD7199	Phase 2
0.7126	Intermediate Similarity	NPD8053	Approved
0.7126	Intermediate Similarity	NPD8054	Approved
0.7118	Intermediate Similarity	NPD3751	Discontinued
0.7115	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD7644	Approved
0.7103	Intermediate Similarity	NPD3705	Approved
0.7103	Intermediate Similarity	NPD1281	Approved
0.7099	Intermediate Similarity	NPD4380	Phase 2
0.7097	Intermediate Similarity	NPD7030	Discontinued
0.7097	Intermediate Similarity	NPD7266	Discontinued
0.7089	Intermediate Similarity	NPD6667	Approved
0.7089	Intermediate Similarity	NPD6666	Approved
0.7086	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD6233	Phase 2
0.7078	Intermediate Similarity	NPD4108	Discontinued
0.7078	Intermediate Similarity	NPD2154	Approved
0.7078	Intermediate Similarity	NPD2155	Approved
0.7078	Intermediate Similarity	NPD2156	Approved
0.7073	Intermediate Similarity	NPD7819	Suspended
0.707	Intermediate Similarity	NPD8166	Discontinued
0.7063	Intermediate Similarity	NPD4319	Phase 2
0.7059	Intermediate Similarity	NPD2157	Approved
0.7059	Intermediate Similarity	NPD968	Approved
0.7055	Intermediate Similarity	NPD2233	Approved
0.7055	Intermediate Similarity	NPD6072	Discontinued
0.7055	Intermediate Similarity	NPD2230	Approved
0.7055	Intermediate Similarity	NPD2232	Approved
0.7052	Intermediate Similarity	NPD7240	Approved
0.7051	Intermediate Similarity	NPD2424	Discontinued
0.7048	Intermediate Similarity	NPD7075	Discontinued
0.7047	Intermediate Similarity	NPD5736	Approved
0.7041	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD1558	Phase 1
0.7037	Intermediate Similarity	NPD3226	Approved
0.7035	Intermediate Similarity	NPD7074	Phase 3
0.7029	Intermediate Similarity	NPD3022	Approved
0.7029	Intermediate Similarity	NPD3021	Approved
0.7019	Intermediate Similarity	NPD7427	Discontinued
0.7018	Intermediate Similarity	NPD7177	Discontinued
0.7012	Intermediate Similarity	NPD5722	Discontinued
0.7011	Intermediate Similarity	NPD7549	Discontinued
0.7007	Intermediate Similarity	NPD1669	Approved
0.7	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD3657	Discovery
0.6987	Remote Similarity	NPD2346	Discontinued
0.6977	Remote Similarity	NPD7054	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