NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	246.13
Volume:	264.072
LogP:	2.919
LogD:	2.486
LogS:	-3.185
# Rotatable Bonds:	1
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.801
Synthetic Accessibility Score:	3.602
Fsp3:	0.4
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.586
MDCK Permeability:	2.077952194667887e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.449
30% Bioavailability (F30%):	0.035

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.713
Plasma Protein Binding (PPB):	85.78771209716797%
Volume Distribution (VD):	1.265
Pgp-substrate:	8.470650672912598%

ADMET: Metabolism

CYP1A2-inhibitor:	0.91
CYP1A2-substrate:	0.678
CYP2C19-inhibitor:	0.623
CYP2C19-substrate:	0.478
CYP2C9-inhibitor:	0.473
CYP2C9-substrate:	0.594
CYP2D6-inhibitor:	0.359
CYP2D6-substrate:	0.23
CYP3A4-inhibitor:	0.735
CYP3A4-substrate:	0.357

ADMET: Excretion

Clearance (CL):	10.196
Half-life (T1/2):	0.312

ADMET: Toxicity

hERG Blockers:	0.047
Human Hepatotoxicity (H-HT):	0.235
Drug-inuced Liver Injury (DILI):	0.234
AMES Toxicity:	0.069
Rat Oral Acute Toxicity:	0.225
Maximum Recommended Daily Dose:	0.313
Skin Sensitization:	0.428
Carcinogencity:	0.272
Eye Corrosion:	0.013
Eye Irritation:	0.744
Respiratory Toxicity:	0.575

Download Data

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

Natural Product: NPC123506

Natural Product ID:	NPC123506
*Common Name:**	3,7-Dihydroxy-3(4H)-Isocadalen-4-One
IUPAC Name:	(2S)-2,6-dihydroxy-4,7-dimethyl-2-propan-2-ylnaphthalen-1-one
Synonyms:
Standard InCHIKey:	KXIUPESKOQTYRQ-OAHLLOKOSA-N
Standard InCHI:	InChI=1S/C15H18O3/c1-8(2)15(18)7-10(4)11-6-13(16)9(3)5-12(11)14(15)17/h5-8,16,18H,1-4H3/t15-/m1/s1
SMILES:	CC(C)[C@@]1(C=C(C)c2cc(c(C)cc2C1=O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL461485
PubChem CID:	642913
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000023] Naphthalenes [CHEMONTID:0002441] Naphthols 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
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
Others	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	57.24	%	PMID[553487]

☑ 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 NPC123506 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	308
0.1-0.2	1575
0.2-0.3	3531
0.3-0.4	9970
0.4-0.5	9361
0.5-0.6	6667
0.6-0.7	8216
0.7-0.8	2673
0.8-0.85	303
0.85-0.9	73
0.9-0.95	15
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9746	High Similarity	NPC282577
0.9664	High Similarity	NPC273683
0.9512	High Similarity	NPC171460
0.9421	High Similarity	NPC199273
0.935	High Similarity	NPC72667
0.9274	High Similarity	NPC96024
0.9268	High Similarity	NPC254492
0.9194	High Similarity	NPC69424
0.9194	High Similarity	NPC84672
0.9194	High Similarity	NPC176130
0.9194	High Similarity	NPC78364
0.9127	High Similarity	NPC108129
0.9127	High Similarity	NPC253488
0.9113	High Similarity	NPC15837
0.9062	High Similarity	NPC78307
0.9048	High Similarity	NPC303910
0.8968	High Similarity	NPC3009
0.8906	High Similarity	NPC471851
0.8898	High Similarity	NPC276238
0.8862	High Similarity	NPC154696
0.8846	High Similarity	NPC202225
0.8837	High Similarity	NPC312560
0.879	High Similarity	NPC307174
0.8788	High Similarity	NPC475957
0.878	High Similarity	NPC190971
0.8769	High Similarity	NPC138472
0.8769	High Similarity	NPC477139
0.8739	High Similarity	NPC242136
0.8722	High Similarity	NPC230811
0.872	High Similarity	NPC275145
0.8712	High Similarity	NPC471670
0.8712	High Similarity	NPC86524
0.8682	High Similarity	NPC198305
0.8682	High Similarity	NPC27659
0.8661	High Similarity	NPC231774
0.8655	High Similarity	NPC231717
0.8651	High Similarity	NPC310540
0.8647	High Similarity	NPC471452
0.8636	High Similarity	NPC22644
0.8629	High Similarity	NPC259703
0.8629	High Similarity	NPC32322
0.8626	High Similarity	NPC263817
0.8626	High Similarity	NPC111845
0.8626	High Similarity	NPC59459
0.8615	High Similarity	NPC41847
0.8605	High Similarity	NPC278928
0.8571	High Similarity	NPC474311
0.8561	High Similarity	NPC50924
0.856	High Similarity	NPC120545
0.855	High Similarity	NPC309430
0.8548	High Similarity	NPC285829
0.8548	High Similarity	NPC206778
0.8538	High Similarity	NPC470725
0.8516	High Similarity	NPC160499
0.8516	High Similarity	NPC474737
0.8507	High Similarity	NPC36868
0.8504	High Similarity	NPC164014
0.8496	Intermediate Similarity	NPC290803
0.8492	Intermediate Similarity	NPC91478
0.8492	Intermediate Similarity	NPC164947
0.8485	Intermediate Similarity	NPC171968
0.8473	Intermediate Similarity	NPC93015
0.8468	Intermediate Similarity	NPC473767
0.8467	Intermediate Similarity	NPC308572
0.8462	Intermediate Similarity	NPC117899
0.845	Intermediate Similarity	NPC324209
0.8443	Intermediate Similarity	NPC322197
0.8438	Intermediate Similarity	NPC137750
0.8425	Intermediate Similarity	NPC135062
0.8403	Intermediate Similarity	NPC95172
0.84	Intermediate Similarity	NPC478121
0.8397	Intermediate Similarity	NPC117609
0.8385	Intermediate Similarity	NPC24869
0.8385	Intermediate Similarity	NPC237225
0.8385	Intermediate Similarity	NPC193203
0.8385	Intermediate Similarity	NPC48248
0.8374	Intermediate Similarity	NPC477453
0.8372	Intermediate Similarity	NPC306765
0.8372	Intermediate Similarity	NPC3224
0.8372	Intermediate Similarity	NPC71610
0.837	Intermediate Similarity	NPC53001
0.837	Intermediate Similarity	NPC264022
0.8359	Intermediate Similarity	NPC68756
0.8359	Intermediate Similarity	NPC152525
0.8359	Intermediate Similarity	NPC474766
0.8359	Intermediate Similarity	NPC142956
0.8359	Intermediate Similarity	NPC173978
0.8358	Intermediate Similarity	NPC153088
0.8358	Intermediate Similarity	NPC80035
0.8358	Intermediate Similarity	NPC283088
0.8346	Intermediate Similarity	NPC267205
0.8346	Intermediate Similarity	NPC52407
0.8346	Intermediate Similarity	NPC53896
0.8346	Intermediate Similarity	NPC176208
0.8346	Intermediate Similarity	NPC4170
0.8346	Intermediate Similarity	NPC254603
0.8333	Intermediate Similarity	NPC244699
0.8333	Intermediate Similarity	NPC239134
0.8333	Intermediate Similarity	NPC474057
0.8333	Intermediate Similarity	NPC248068
0.8333	Intermediate Similarity	NPC241001
0.8333	Intermediate Similarity	NPC18798
0.8321	Intermediate Similarity	NPC34414
0.8321	Intermediate Similarity	NPC99731
0.8321	Intermediate Similarity	NPC146647
0.8321	Intermediate Similarity	NPC169452
0.8321	Intermediate Similarity	NPC181560
0.8309	Intermediate Similarity	NPC87723
0.8309	Intermediate Similarity	NPC13715
0.8308	Intermediate Similarity	NPC19432
0.8306	Intermediate Similarity	NPC174087
0.8306	Intermediate Similarity	NPC160199
0.8305	Intermediate Similarity	NPC21594
0.8296	Intermediate Similarity	NPC254847
0.8296	Intermediate Similarity	NPC315275
0.8296	Intermediate Similarity	NPC191976
0.8295	Intermediate Similarity	NPC477454
0.8293	Intermediate Similarity	NPC161304
0.8286	Intermediate Similarity	NPC478160
0.8284	Intermediate Similarity	NPC12070
0.8284	Intermediate Similarity	NPC218854
0.8284	Intermediate Similarity	NPC52368
0.8284	Intermediate Similarity	NPC166480
0.8284	Intermediate Similarity	NPC282780
0.8281	Intermediate Similarity	NPC174991
0.8281	Intermediate Similarity	NPC471187
0.8271	Intermediate Similarity	NPC183103
0.8271	Intermediate Similarity	NPC58685
0.8268	Intermediate Similarity	NPC249340
0.8268	Intermediate Similarity	NPC162935
0.8268	Intermediate Similarity	NPC25168
0.8261	Intermediate Similarity	NPC110810
0.8258	Intermediate Similarity	NPC62219
0.8248	Intermediate Similarity	NPC242994
0.8248	Intermediate Similarity	NPC162939
0.8248	Intermediate Similarity	NPC138099
0.8244	Intermediate Similarity	NPC179898
0.8244	Intermediate Similarity	NPC229894
0.8244	Intermediate Similarity	NPC282923
0.824	Intermediate Similarity	NPC328694
0.824	Intermediate Similarity	NPC474890
0.824	Intermediate Similarity	NPC161943
0.824	Intermediate Similarity	NPC273282
0.8235	Intermediate Similarity	NPC226699
0.8235	Intermediate Similarity	NPC53414
0.8235	Intermediate Similarity	NPC228737
0.8235	Intermediate Similarity	NPC471905
0.8235	Intermediate Similarity	NPC53206
0.8235	Intermediate Similarity	NPC277559
0.8231	Intermediate Similarity	NPC1991
0.8231	Intermediate Similarity	NPC51037
0.8231	Intermediate Similarity	NPC473691
0.8226	Intermediate Similarity	NPC83718
0.8226	Intermediate Similarity	NPC108288
0.8222	Intermediate Similarity	NPC258502
0.8222	Intermediate Similarity	NPC249272
0.8217	Intermediate Similarity	NPC181334
0.8217	Intermediate Similarity	NPC74507
0.8217	Intermediate Similarity	NPC234890
0.8211	Intermediate Similarity	NPC186933
0.8209	Intermediate Similarity	NPC48036
0.8209	Intermediate Similarity	NPC225051
0.8209	Intermediate Similarity	NPC115458
0.8209	Intermediate Similarity	NPC114183
0.8209	Intermediate Similarity	NPC37299
0.8209	Intermediate Similarity	NPC180261
0.8203	Intermediate Similarity	NPC11250
0.8203	Intermediate Similarity	NPC121168
0.8203	Intermediate Similarity	NPC300274
0.8201	Intermediate Similarity	NPC201297
0.8201	Intermediate Similarity	NPC193555
0.8195	Intermediate Similarity	NPC72669
0.8195	Intermediate Similarity	NPC279596
0.8195	Intermediate Similarity	NPC85342
0.8195	Intermediate Similarity	NPC474517
0.8195	Intermediate Similarity	NPC164295
0.8195	Intermediate Similarity	NPC17083
0.8189	Intermediate Similarity	NPC165197
0.8189	Intermediate Similarity	NPC216216
0.8188	Intermediate Similarity	NPC471853
0.8182	Intermediate Similarity	NPC92624
0.8175	Intermediate Similarity	NPC61398
0.8175	Intermediate Similarity	NPC416
0.8175	Intermediate Similarity	NPC173980
0.8175	Intermediate Similarity	NPC4214
0.8169	Intermediate Similarity	NPC5568
0.8162	Intermediate Similarity	NPC475549
0.8162	Intermediate Similarity	NPC118919
0.8162	Intermediate Similarity	NPC38158
0.8154	Intermediate Similarity	NPC131799
0.8154	Intermediate Similarity	NPC475733
0.8151	Intermediate Similarity	NPC6984
0.8148	Intermediate Similarity	NPC270899
0.8148	Intermediate Similarity	NPC474519
0.8143	Intermediate Similarity	NPC100242
0.8143	Intermediate Similarity	NPC478164
0.814	Intermediate Similarity	NPC375356
0.8134	Intermediate Similarity	NPC175738
0.8134	Intermediate Similarity	NPC88864
0.8134	Intermediate Similarity	NPC165612

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 NPC123506 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	331
0.1-0.2	961
0.2-0.3	1444
0.3-0.4	2706
0.4-0.5	2071
0.5-0.6	1112
0.6-0.7	448
0.7-0.8	72
0.8-0.85	5
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.832	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.8296	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8226	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD1201	Approved
0.811	Intermediate Similarity	NPD2932	Approved
0.8015	Intermediate Similarity	NPD1470	Approved
0.7969	Intermediate Similarity	NPD3019	Approved
0.7832	Intermediate Similarity	NPD7390	Discontinued
0.777	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7762	Intermediate Similarity	NPD3300	Phase 2
0.7714	Intermediate Similarity	NPD5404	Approved
0.7714	Intermediate Similarity	NPD5406	Approved
0.7714	Intermediate Similarity	NPD5408	Approved
0.7714	Intermediate Similarity	NPD5405	Approved
0.7643	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7612	Intermediate Similarity	NPD1164	Approved
0.7537	Intermediate Similarity	NPD1283	Approved
0.75	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7003	Approved
0.7482	Intermediate Similarity	NPD943	Approved
0.7481	Intermediate Similarity	NPD1651	Approved
0.748	Intermediate Similarity	NPD7635	Approved
0.7479	Intermediate Similarity	NPD288	Approved
0.7424	Intermediate Similarity	NPD4626	Approved
0.7415	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7395	Intermediate Similarity	NPD844	Approved
0.7388	Intermediate Similarity	NPD3972	Approved
0.7381	Intermediate Similarity	NPD4750	Phase 3
0.7376	Intermediate Similarity	NPD1607	Approved
0.7368	Intermediate Similarity	NPD3023	Approved
0.7368	Intermediate Similarity	NPD3026	Approved
0.7364	Intermediate Similarity	NPD5951	Approved
0.7361	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7348	Intermediate Similarity	NPD3024	Approved
0.7348	Intermediate Similarity	NPD3025	Approved
0.7343	Intermediate Similarity	NPD2935	Discontinued
0.7323	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7313	Intermediate Similarity	NPD1281	Approved
0.7292	Intermediate Similarity	NPD2346	Discontinued
0.7273	Intermediate Similarity	NPD2799	Discontinued
0.7273	Intermediate Similarity	NPD9545	Approved
0.7266	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD1809	Phase 2
0.7234	Intermediate Similarity	NPD1240	Approved
0.7227	Intermediate Similarity	NPD845	Approved
0.7222	Intermediate Similarity	NPD2342	Discontinued
0.7222	Intermediate Similarity	NPD6100	Approved
0.7222	Intermediate Similarity	NPD6099	Approved
0.7219	Intermediate Similarity	NPD7458	Discontinued
0.7214	Intermediate Similarity	NPD3764	Approved
0.7213	Intermediate Similarity	NPD3020	Approved
0.7206	Intermediate Similarity	NPD1755	Approved
0.7181	Intermediate Similarity	NPD2533	Approved
0.7181	Intermediate Similarity	NPD2534	Approved
0.7181	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD2532	Approved
0.7174	Intermediate Similarity	NPD2798	Approved
0.7172	Intermediate Similarity	NPD2344	Approved
0.7165	Intermediate Similarity	NPD9266	Approved
0.7165	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD74	Approved
0.7164	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD6663	Approved
0.7153	Intermediate Similarity	NPD1876	Approved
0.7143	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD8166	Discontinued
0.7122	Intermediate Similarity	NPD5736	Approved
0.7121	Intermediate Similarity	NPD9493	Approved
0.712	Intermediate Similarity	NPD1237	Approved
0.7105	Intermediate Similarity	NPD3226	Approved
0.709	Intermediate Similarity	NPD5691	Approved
0.7087	Intermediate Similarity	NPD9264	Approved
0.7087	Intermediate Similarity	NPD9263	Approved
0.7087	Intermediate Similarity	NPD9267	Approved
0.7075	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD1471	Phase 3
0.704	Intermediate Similarity	NPD1930	Approved
0.704	Intermediate Similarity	NPD1929	Approved
0.704	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD4059	Approved
0.7037	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD1510	Phase 2
0.7032	Intermediate Similarity	NPD7819	Suspended
0.7027	Intermediate Similarity	NPD3750	Approved
0.7025	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD7473	Discontinued
0.7016	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD3091	Approved
0.7007	Intermediate Similarity	NPD4878	Approved
0.7007	Intermediate Similarity	NPD9269	Phase 2
0.7	Intermediate Similarity	NPD9494	Approved
0.6993	Remote Similarity	NPD4060	Phase 1
0.6993	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD6959	Discontinued
0.698	Remote Similarity	NPD2309	Approved
0.6977	Remote Similarity	NPD3021	Approved
0.6977	Remote Similarity	NPD3022	Approved
0.6967	Remote Similarity	NPD2860	Approved
0.6967	Remote Similarity	NPD2859	Approved
0.6963	Remote Similarity	NPD9268	Approved
0.6957	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD6232	Discontinued
0.6935	Remote Similarity	NPD2066	Phase 3
0.6913	Remote Similarity	NPD4628	Phase 3
0.6908	Remote Similarity	NPD6273	Approved
0.6905	Remote Similarity	NPD8150	Discontinued
0.6897	Remote Similarity	NPD6651	Approved
0.6894	Remote Similarity	NPD1241	Discontinued
0.6885	Remote Similarity	NPD2934	Approved
0.6885	Remote Similarity	NPD2933	Approved
0.6884	Remote Similarity	NPD1608	Approved
0.6875	Remote Similarity	NPD2979	Phase 3
0.6861	Remote Similarity	NPD4879	Approved
0.6846	Remote Similarity	NPD2800	Approved
0.6828	Remote Similarity	NPD230	Phase 1
0.6825	Remote Similarity	NPD846	Approved
0.6825	Remote Similarity	NPD940	Approved
0.6821	Remote Similarity	NPD7236	Approved
0.6815	Remote Similarity	NPD7610	Discontinued
0.6815	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD3092	Approved
0.6803	Remote Similarity	NPD4308	Phase 3
0.6797	Remote Similarity	NPD1512	Approved
0.6792	Remote Similarity	NPD7075	Discontinued
0.6788	Remote Similarity	NPD2286	Discontinued
0.6788	Remote Similarity	NPD1751	Approved
0.6779	Remote Similarity	NPD1549	Phase 2
0.6774	Remote Similarity	NPD3495	Discontinued
0.6772	Remote Similarity	NPD9261	Approved
0.6772	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6767	Remote Similarity	NPD1398	Phase 1
0.6761	Remote Similarity	NPD4208	Discontinued
0.6741	Remote Similarity	NPD7325	Clinical (unspecified phase)
0.6741	Remote Similarity	NPD7340	Approved
0.6738	Remote Similarity	NPD2797	Approved
0.6736	Remote Similarity	NPD411	Approved
0.6736	Remote Similarity	NPD3268	Approved
0.6736	Remote Similarity	NPD2313	Discontinued
0.6731	Remote Similarity	NPD6599	Discontinued
0.6731	Remote Similarity	NPD4380	Phase 2
0.673	Remote Similarity	NPD3882	Suspended
0.6727	Remote Similarity	NPD5844	Phase 1
0.6727	Remote Similarity	NPD6020	Phase 2
0.6721	Remote Similarity	NPD7631	Approved
0.6718	Remote Similarity	NPD1792	Phase 2
0.6716	Remote Similarity	NPD9281	Approved
0.6716	Remote Similarity	NPD497	Approved
0.6715	Remote Similarity	NPD4093	Discontinued
0.6714	Remote Similarity	NPD4749	Approved
0.6711	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.671	Remote Similarity	NPD7239	Suspended
0.6709	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD5027	Approved
0.6707	Remote Similarity	NPD5031	Approved
0.6707	Remote Similarity	NPD5029	Approved
0.669	Remote Similarity	NPD8032	Phase 2
0.6689	Remote Similarity	NPD3748	Approved
0.6688	Remote Similarity	NPD5049	Phase 3
0.6667	Remote Similarity	NPD5026	Approved
0.6667	Remote Similarity	NPD4625	Phase 3
0.6667	Remote Similarity	NPD7008	Discontinued
0.6667	Remote Similarity	NPD3095	Discontinued
0.6667	Remote Similarity	NPD5028	Approved
0.6667	Remote Similarity	NPD1511	Approved
0.6667	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD36	Approved
0.6667	Remote Similarity	NPD4955	Approved
0.6667	Remote Similarity	NPD6696	Suspended
0.6667	Remote Similarity	NPD17	Approved
0.6667	Remote Similarity	NPD256	Approved
0.6667	Remote Similarity	NPD5034	Approved
0.6667	Remote Similarity	NPD255	Approved
0.6667	Remote Similarity	NPD4954	Approved
0.6647	Remote Similarity	NPD5968	Phase 3
0.6647	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD2354	Approved
0.6645	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD4477	Approved
0.6644	Remote Similarity	NPD2531	Phase 2
0.6644	Remote Similarity	NPD4476	Approved
0.6644	Remote Similarity	NPD2796	Approved
0.6644	Remote Similarity	NPD2438	Suspended
0.6643	Remote Similarity	NPD9717	Approved
0.6642	Remote Similarity	NPD496	Approved
0.6642	Remote Similarity	NPD7009	Phase 2
0.6642	Remote Similarity	NPD495	Approved
0.6642	Remote Similarity	NPD2234	Approved
0.6642	Remote Similarity	NPD2229	Approved
0.6642	Remote Similarity	NPD2228	Approved
0.6642	Remote Similarity	NPD498	Approved
0.6639	Remote Similarity	NPD7609	Phase 3
0.6627	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6626	Remote Similarity	NPD5710	Approved
0.6626	Remote Similarity	NPD5711	Approved
0.6623	Remote Similarity	NPD1243	Approved
0.662	Remote Similarity	NPD3094	Phase 2
0.662	Remote Similarity	NPD1203	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