NPASS Compound

Structure

CID212207 OpenBabel06191716002D 26 29 0 0 1 0 0 0 0 0999 V2000 2.5209 -1.4896 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3579 -2.0822 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6808 3.9145 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5512 3.4118 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5197 1.4538 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6800 0.9690 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8395 2.4248 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0008 2.9096 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5200 2.4239 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8395 -0.4850 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3594 0.0010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5206 -0.4843 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6376 -1.4332 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8406 1.4543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8397 1.4548 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8408 2.4244 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6803 0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0003 0.9695 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6800 0.9700 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8403 -0.4848 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6805 2.9092 0.0000 C 0 0 0 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 0.2845 -1.7326 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8406 -1.4848 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0003 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3591 0.9704 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 13 1 0 0 0 0 3 21 1 0 0 0 0 4 21 1 0 0 0 0 5 6 1 0 0 0 0 5 9 1 0 0 0 0 6 14 1 0 0 0 0 7 8 2 0 0 0 0 7 15 1 0 0 0 0 8 16 1 0 0 0 0 9 21 1 0 0 0 0 10 13 1 0 0 0 0 10 22 1 0 0 0 0 11 12 1 0 0 0 0 11 26 1 0 0 0 0 12 1 1 6 0 0 0 12 17 1 0 0 0 0 13 23 2 0 0 0 0 14 16 2 0 0 0 0 14 18 1 0 0 0 0 15 18 2 0 0 0 0 15 19 1 0 0 0 0 16 21 1 0 0 0 0 17 19 2 0 0 0 0 17 20 1 0 0 0 0 18 22 1 0 0 0 0 19 26 1 0 0 0 0 20 22 1 0 0 0 0 20 24 2 0 0 0 0 22 25 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	354.18
Volume:	374.184
LogP:	4.202
LogD:	3.477
LogS:	-4.912
# Rotatable Bonds:	2
TPSA:	63.6
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.884
Synthetic Accessibility Score:	4.177
Fsp3:	0.545
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.902
MDCK Permeability:	2.508246325305663e-05
Pgp-inhibitor:	0.99
Pgp-substrate:	0.044
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.923
30% Bioavailability (F30%):	0.544

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.482
Plasma Protein Binding (PPB):	95.54344940185547%
Volume Distribution (VD):	1.548
Pgp-substrate:	5.74217414855957%

ADMET: Metabolism

CYP1A2-inhibitor:	0.938
CYP1A2-substrate:	0.692
CYP2C19-inhibitor:	0.933
CYP2C19-substrate:	0.821
CYP2C9-inhibitor:	0.767
CYP2C9-substrate:	0.191
CYP2D6-inhibitor:	0.907
CYP2D6-substrate:	0.133
CYP3A4-inhibitor:	0.885
CYP3A4-substrate:	0.683

ADMET: Excretion

Clearance (CL):	0.909
Half-life (T1/2):	0.033

ADMET: Toxicity

hERG Blockers:	0.033
Human Hepatotoxicity (H-HT):	0.328
Drug-inuced Liver Injury (DILI):	0.221
AMES Toxicity:	0.118
Rat Oral Acute Toxicity:	0.717
Maximum Recommended Daily Dose:	0.953
Skin Sensitization:	0.278
Carcinogencity:	0.287
Eye Corrosion:	0.003
Eye Irritation:	0.02
Respiratory Toxicity:	0.753

Download Data

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

Natural Product: NPC212207

Natural Product ID:	NPC212207
*Common Name:**	(1R,10S)-10-Hydroxy-1,6,6-Trimethyl-10-(2-Oxopropyl)-1,2,6,7,8,9-Hexahydrophenanthro[1,2-B]Furan-11(10H)-One
IUPAC Name:	(1R,10S)-10-hydroxy-1,6,6-trimethyl-10-(2-oxopropyl)-2,7,8,9-tetrahydro-1H-naphtho[1,2-g][1]benzofuran-11-one
Synonyms:
Standard InCHIKey:	KZLPKGGMSDHTRS-YTEVENLXSA-N
Standard InCHI:	InChI=1S/C22H26O4/c1-12-11-26-19-15-7-8-16-14(6-5-9-21(16,3)4)18(15)22(25,10-13(2)23)20(24)17(12)19/h7-8,12,25H,5-6,9-11H2,1-4H3/t12-,22-/m0/s1
SMILES:	CC(=O)C[C@@]1(O)C(=O)C2=C(c3c1c1CCCC(c1cc3)(C)C)OC[C@@H]2C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2261307
PubChem CID:	3083515
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0002548] Tanshinones, isotanshinones, 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
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	root	n.a.	PMID[11374966]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16038550]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17583950]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18855446]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20455578]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21775156]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23286284]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24108414]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27569393]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29185738]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30351923]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	root	n.a.	PMID[3655791]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	roots	n.a.	n.a.	PMID[9834151]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT68	Individual Protein	Aldose reductase	Rattus norvegicus	IC50	=	1737.8	nM	PMID[473830]

☑ 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 NPC212207 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	288
0.1-0.2	1222
0.2-0.3	2369
0.3-0.4	5987
0.4-0.5	11976
0.5-0.6	10379
0.6-0.7	9281
0.7-0.8	1180
0.8-0.85	9
0.85-0.9	4
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9615	High Similarity	NPC309056
0.8881	High Similarity	NPC310662
0.855	High Similarity	NPC51079
0.8527	High Similarity	NPC77000
0.8527	High Similarity	NPC238861
0.8286	Intermediate Similarity	NPC475549
0.8175	Intermediate Similarity	NPC49272
0.8169	Intermediate Similarity	NPC475104
0.8143	Intermediate Similarity	NPC23894
0.8106	Intermediate Similarity	NPC988
0.8106	Intermediate Similarity	NPC289432
0.8074	Intermediate Similarity	NPC295664
0.8045	Intermediate Similarity	NPC144547
0.8043	Intermediate Similarity	NPC471832
0.8042	Intermediate Similarity	NPC476643
0.8029	Intermediate Similarity	NPC51448
0.8029	Intermediate Similarity	NPC115797
0.8027	Intermediate Similarity	NPC474630
0.8015	Intermediate Similarity	NPC222968
0.8015	Intermediate Similarity	NPC80605
0.8015	Intermediate Similarity	NPC323440
0.8014	Intermediate Similarity	NPC474659
0.7987	Intermediate Similarity	NPC306799
0.7987	Intermediate Similarity	NPC101043
0.7972	Intermediate Similarity	NPC156888
0.7972	Intermediate Similarity	NPC470721
0.7972	Intermediate Similarity	NPC6100
0.7972	Intermediate Similarity	NPC119542
0.7972	Intermediate Similarity	NPC470722
0.7956	Intermediate Similarity	NPC253681
0.7956	Intermediate Similarity	NPC5486
0.7931	Intermediate Similarity	NPC183540
0.7891	Intermediate Similarity	NPC127857
0.7883	Intermediate Similarity	NPC236405
0.7881	Intermediate Similarity	NPC248265
0.7881	Intermediate Similarity	NPC11588
0.7881	Intermediate Similarity	NPC134685
0.7881	Intermediate Similarity	NPC229545
0.7877	Intermediate Similarity	NPC283292
0.7872	Intermediate Similarity	NPC476644
0.7872	Intermediate Similarity	NPC165612
0.7868	Intermediate Similarity	NPC307139
0.7868	Intermediate Similarity	NPC328107
0.7867	Intermediate Similarity	NPC471103
0.7867	Intermediate Similarity	NPC51602
0.7863	Intermediate Similarity	NPC135730
0.7838	Intermediate Similarity	NPC29932
0.7838	Intermediate Similarity	NPC477409
0.7838	Intermediate Similarity	NPC471451
0.7836	Intermediate Similarity	NPC232958
0.7829	Intermediate Similarity	NPC114357
0.7829	Intermediate Similarity	NPC259144
0.7829	Intermediate Similarity	NPC155329
0.782	Intermediate Similarity	NPC254233
0.7808	Intermediate Similarity	NPC136649
0.78	Intermediate Similarity	NPC112216
0.78	Intermediate Similarity	NPC198455
0.78	Intermediate Similarity	NPC165260
0.78	Intermediate Similarity	NPC161239
0.7786	Intermediate Similarity	NPC228936
0.7786	Intermediate Similarity	NPC131684
0.7786	Intermediate Similarity	NPC93181
0.7778	Intermediate Similarity	NPC38158
0.777	Intermediate Similarity	NPC471107
0.777	Intermediate Similarity	NPC476473
0.777	Intermediate Similarity	NPC471100
0.777	Intermediate Similarity	NPC143898
0.777	Intermediate Similarity	NPC469885
0.7769	Intermediate Similarity	NPC143768
0.7763	Intermediate Similarity	NPC219419
0.7761	Intermediate Similarity	NPC204784
0.7754	Intermediate Similarity	NPC9180
0.7754	Intermediate Similarity	NPC100402
0.7748	Intermediate Similarity	NPC197037
0.7744	Intermediate Similarity	NPC45794
0.774	Intermediate Similarity	NPC213567
0.7737	Intermediate Similarity	NPC77691
0.7737	Intermediate Similarity	NPC472704
0.7736	Intermediate Similarity	NPC316262
0.7736	Intermediate Similarity	NPC314653
0.7733	Intermediate Similarity	NPC81698
0.7733	Intermediate Similarity	NPC60509
0.7733	Intermediate Similarity	NPC250046
0.7718	Intermediate Similarity	NPC475813
0.7712	Intermediate Similarity	NPC21410
0.7712	Intermediate Similarity	NPC282239
0.7712	Intermediate Similarity	NPC473670
0.7708	Intermediate Similarity	NPC472551
0.7708	Intermediate Similarity	NPC472545
0.7703	Intermediate Similarity	NPC201297
0.7703	Intermediate Similarity	NPC474300
0.7698	Intermediate Similarity	NPC81135
0.7692	Intermediate Similarity	NPC67197
0.7687	Intermediate Similarity	NPC42262
0.7687	Intermediate Similarity	NPC472546
0.7687	Intermediate Similarity	NPC318173
0.7687	Intermediate Similarity	NPC327916
0.7687	Intermediate Similarity	NPC241349
0.7687	Intermediate Similarity	NPC147542
0.7687	Intermediate Similarity	NPC32749
0.7687	Intermediate Similarity	NPC37992
0.7687	Intermediate Similarity	NPC220496
0.7682	Intermediate Similarity	NPC7095
0.7682	Intermediate Similarity	NPC91730
0.7677	Intermediate Similarity	NPC3898
0.7676	Intermediate Similarity	NPC209851
0.7671	Intermediate Similarity	NPC472547
0.7669	Intermediate Similarity	NPC105141
0.7669	Intermediate Similarity	NPC242764
0.7667	Intermediate Similarity	NPC474309
0.7667	Intermediate Similarity	NPC132652
0.7667	Intermediate Similarity	NPC217918
0.7667	Intermediate Similarity	NPC475923
0.7664	Intermediate Similarity	NPC273336
0.7664	Intermediate Similarity	NPC182333
0.7664	Intermediate Similarity	NPC472703
0.7664	Intermediate Similarity	NPC65627
0.7662	Intermediate Similarity	NPC11410
0.7662	Intermediate Similarity	NPC106895
0.7655	Intermediate Similarity	NPC474311
0.7655	Intermediate Similarity	NPC39549
0.7652	Intermediate Similarity	NPC474095
0.7652	Intermediate Similarity	NPC221275
0.7652	Intermediate Similarity	NPC474408
0.7647	Intermediate Similarity	NPC472981
0.7647	Intermediate Similarity	NPC77719
0.7643	Intermediate Similarity	NPC268607
0.7639	Intermediate Similarity	NPC477893
0.7635	Intermediate Similarity	NPC257003
0.7635	Intermediate Similarity	NPC124365
0.7634	Intermediate Similarity	NPC13784
0.7632	Intermediate Similarity	NPC470153
0.7632	Intermediate Similarity	NPC470479
0.7626	Intermediate Similarity	NPC294050
0.7626	Intermediate Similarity	NPC328997
0.7622	Intermediate Similarity	NPC88864
0.7622	Intermediate Similarity	NPC312560
0.7622	Intermediate Similarity	NPC309430
0.7622	Intermediate Similarity	NPC477407
0.7622	Intermediate Similarity	NPC477406
0.7619	Intermediate Similarity	NPC216312
0.7619	Intermediate Similarity	NPC111422
0.7619	Intermediate Similarity	NPC477408
0.7619	Intermediate Similarity	NPC471602
0.7619	Intermediate Similarity	NPC256463
0.7619	Intermediate Similarity	NPC476477
0.7619	Intermediate Similarity	NPC29771
0.7619	Intermediate Similarity	NPC299405
0.7619	Intermediate Similarity	NPC306835
0.7619	Intermediate Similarity	NPC1268
0.7616	Intermediate Similarity	NPC300540
0.7616	Intermediate Similarity	NPC136878
0.7613	Intermediate Similarity	NPC472393
0.761	Intermediate Similarity	NPC475106
0.7609	Intermediate Similarity	NPC85511
0.7609	Intermediate Similarity	NPC12881
0.7609	Intermediate Similarity	NPC318067
0.7609	Intermediate Similarity	NPC140118
0.7606	Intermediate Similarity	NPC291419
0.7606	Intermediate Similarity	NPC60825
0.7606	Intermediate Similarity	NPC253488
0.7606	Intermediate Similarity	NPC475741
0.7603	Intermediate Similarity	NPC118366
0.76	Intermediate Similarity	NPC274085
0.76	Intermediate Similarity	NPC471600
0.76	Intermediate Similarity	NPC169942
0.76	Intermediate Similarity	NPC89664
0.76	Intermediate Similarity	NPC469513
0.7597	Intermediate Similarity	NPC228204
0.7597	Intermediate Similarity	NPC112523
0.7597	Intermediate Similarity	NPC26033
0.7597	Intermediate Similarity	NPC114410
0.7597	Intermediate Similarity	NPC472549
0.7595	Intermediate Similarity	NPC313368
0.7595	Intermediate Similarity	NPC284495
0.7594	Intermediate Similarity	NPC471616
0.7594	Intermediate Similarity	NPC226093
0.7591	Intermediate Similarity	NPC293831
0.7591	Intermediate Similarity	NPC369
0.7586	Intermediate Similarity	NPC472372
0.7586	Intermediate Similarity	NPC472374
0.7584	Intermediate Similarity	NPC308572
0.7582	Intermediate Similarity	NPC469647
0.7582	Intermediate Similarity	NPC22571
0.7582	Intermediate Similarity	NPC138641
0.7582	Intermediate Similarity	NPC283875
0.7582	Intermediate Similarity	NPC469648
0.7576	Intermediate Similarity	NPC196075
0.7576	Intermediate Similarity	NPC326664
0.7571	Intermediate Similarity	NPC474106
0.7571	Intermediate Similarity	NPC169913
0.7571	Intermediate Similarity	NPC146239
0.7571	Intermediate Similarity	NPC51292
0.7569	Intermediate Similarity	NPC59459
0.7569	Intermediate Similarity	NPC254603
0.7569	Intermediate Similarity	NPC48929
0.7569	Intermediate Similarity	NPC136994
0.7569	Intermediate Similarity	NPC329913
0.7569	Intermediate Similarity	NPC88255
0.7569	Intermediate Similarity	NPC193169

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 NPC212207 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	258
0.1-0.2	848
0.2-0.3	1482
0.3-0.4	2731
0.4-0.5	2305
0.5-0.6	1198
0.6-0.7	317
0.7-0.8	10
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
0.8527	High Similarity	NPD3412	Clinical (unspecified phase)
0.7535	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD7236	Approved
0.7355	Intermediate Similarity	NPD3226	Approved
0.7293	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD7239	Suspended
0.7235	Intermediate Similarity	NPD8434	Phase 2
0.72	Intermediate Similarity	NPD2346	Discontinued
0.7174	Intermediate Similarity	NPD7741	Discontinued
0.7172	Intermediate Similarity	NPD7008	Discontinued
0.7132	Intermediate Similarity	NPD5951	Approved
0.7132	Intermediate Similarity	NPD2629	Approved
0.7132	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD7799	Discontinued
0.7097	Intermediate Similarity	NPD2533	Approved
0.7097	Intermediate Similarity	NPD2532	Approved
0.7097	Intermediate Similarity	NPD2534	Approved
0.7097	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD4198	Discontinued
0.7075	Intermediate Similarity	NPD7961	Discontinued
0.7071	Intermediate Similarity	NPD2932	Approved
0.7035	Intermediate Similarity	NPD8150	Discontinued
0.7021	Intermediate Similarity	NPD7457	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD6100	Approved
0.702	Intermediate Similarity	NPD6099	Approved
0.7014	Intermediate Similarity	NPD1470	Approved
0.7007	Intermediate Similarity	NPD3764	Approved
0.6993	Remote Similarity	NPD2800	Approved
0.6968	Remote Similarity	NPD3300	Phase 2
0.6963	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD3317	Approved
0.695	Remote Similarity	NPD5125	Phase 3
0.695	Remote Similarity	NPD3019	Approved
0.695	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.695	Remote Similarity	NPD5126	Approved
0.6948	Remote Similarity	NPD4628	Phase 3
0.6948	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD7473	Discontinued
0.6941	Remote Similarity	NPD8368	Discontinued
0.694	Remote Similarity	NPD2182	Approved
0.6919	Remote Similarity	NPD8407	Phase 2
0.6913	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD6959	Discontinued
0.6892	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD2067	Discontinued
0.6879	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD7058	Phase 2
0.6871	Remote Similarity	NPD7057	Phase 3
0.6867	Remote Similarity	NPD6232	Discontinued
0.6863	Remote Similarity	NPD1471	Phase 3
0.6853	Remote Similarity	NPD1201	Approved
0.6852	Remote Similarity	NPD5761	Phase 2
0.6852	Remote Similarity	NPD7819	Suspended
0.6852	Remote Similarity	NPD5760	Phase 2
0.6842	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD8166	Discontinued
0.6839	Remote Similarity	NPD7003	Approved
0.6838	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD1283	Approved
0.6828	Remote Similarity	NPD6696	Suspended
0.6815	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.68	Remote Similarity	NPD2979	Phase 3
0.6779	Remote Similarity	NPD2313	Discontinued
0.6774	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.677	Remote Similarity	NPD6599	Discontinued
0.6767	Remote Similarity	NPD5909	Discontinued
0.6761	Remote Similarity	NPD8360	Approved
0.6761	Remote Similarity	NPD8361	Approved
0.6761	Remote Similarity	NPD1651	Approved
0.6753	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD6085	Phase 2
0.6733	Remote Similarity	NPD6663	Approved
0.6732	Remote Similarity	NPD2799	Discontinued
0.673	Remote Similarity	NPD6273	Approved
0.6711	Remote Similarity	NPD6651	Approved
0.6708	Remote Similarity	NPD7458	Discontinued
0.6707	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD3751	Discontinued
0.6704	Remote Similarity	NPD6534	Approved
0.6704	Remote Similarity	NPD6535	Approved
0.6691	Remote Similarity	NPD6010	Discontinued
0.669	Remote Similarity	NPD3972	Approved
0.669	Remote Similarity	NPD4878	Approved
0.669	Remote Similarity	NPD1608	Approved
0.6689	Remote Similarity	NPD5736	Approved
0.6688	Remote Similarity	NPD2935	Discontinued
0.6687	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3026	Approved
0.6667	Remote Similarity	NPD8435	Approved
0.6667	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4380	Phase 2
0.6667	Remote Similarity	NPD3023	Approved
0.6667	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD5494	Approved
0.6646	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD3024	Approved
0.6643	Remote Similarity	NPD3025	Approved
0.6642	Remote Similarity	NPD1237	Approved
0.6642	Remote Similarity	NPD164	Approved
0.6627	Remote Similarity	NPD7075	Discontinued
0.6623	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD8032	Phase 2
0.6623	Remote Similarity	NPD7305	Phase 1
0.6623	Remote Similarity	NPD7033	Discontinued
0.6623	Remote Similarity	NPD1510	Phase 2
0.6622	Remote Similarity	NPD2798	Approved
0.6621	Remote Similarity	NPD1281	Approved
0.6621	Remote Similarity	NPD6287	Discontinued
0.662	Remote Similarity	NPD7610	Discontinued
0.6619	Remote Similarity	NPD7094	Approved
0.6619	Remote Similarity	NPD6858	Approved
0.6612	Remote Similarity	NPD6778	Approved
0.6612	Remote Similarity	NPD6781	Approved
0.6612	Remote Similarity	NPD6780	Approved
0.6612	Remote Similarity	NPD6776	Approved
0.6612	Remote Similarity	NPD6782	Approved
0.6612	Remote Similarity	NPD6777	Approved
0.6612	Remote Similarity	NPD6779	Approved
0.6605	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD7390	Discontinued
0.6604	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6603	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6601	Remote Similarity	NPD1607	Approved
0.6599	Remote Similarity	NPD1876	Approved
0.6593	Remote Similarity	NPD7700	Phase 2
0.6593	Remote Similarity	NPD7699	Phase 2
0.6591	Remote Similarity	NPD2066	Phase 3
0.6585	Remote Similarity	NPD6801	Discontinued
0.6582	Remote Similarity	NPD6190	Approved
0.6581	Remote Similarity	NPD5408	Approved
0.6581	Remote Similarity	NPD5404	Approved
0.6581	Remote Similarity	NPD5405	Approved
0.6581	Remote Similarity	NPD5406	Approved
0.6573	Remote Similarity	NPD7009	Phase 2
0.6571	Remote Similarity	NPD8312	Approved
0.6571	Remote Similarity	NPD8313	Approved
0.657	Remote Similarity	NPD5844	Phase 1
0.657	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6568	Remote Similarity	NPD5711	Approved
0.6568	Remote Similarity	NPD5710	Approved
0.6566	Remote Similarity	NPD3882	Suspended
0.6565	Remote Similarity	NPD3495	Discontinued
0.6564	Remote Similarity	NPD7028	Phase 2
0.6556	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD3268	Approved
0.6552	Remote Similarity	NPD4879	Approved
0.6552	Remote Similarity	NPD6764	Approved
0.6552	Remote Similarity	NPD6765	Approved
0.6549	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD2801	Approved
0.6538	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD6002	Phase 3
0.6538	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD8485	Approved
0.6538	Remote Similarity	NPD2344	Approved
0.6538	Remote Similarity	NPD6005	Phase 3
0.6538	Remote Similarity	NPD6004	Phase 3
0.6533	Remote Similarity	NPD7055	Discontinued
0.6524	Remote Similarity	NPD7411	Suspended
0.6519	Remote Similarity	NPD3750	Approved
0.651	Remote Similarity	NPD2788	Approved
0.651	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6506	Remote Similarity	NPD5402	Approved
0.6505	Remote Similarity	NPD7697	Approved
0.6505	Remote Similarity	NPD7435	Discontinued
0.6505	Remote Similarity	NPD7696	Phase 3
0.6505	Remote Similarity	NPD7698	Approved
0.6497	Remote Similarity	NPD1549	Phase 2
0.649	Remote Similarity	NPD4625	Phase 3
0.6485	Remote Similarity	NPD37	Approved
0.6485	Remote Similarity	NPD1934	Approved
0.6483	Remote Similarity	NPD5306	Approved
0.6483	Remote Similarity	NPD4626	Approved
0.6483	Remote Similarity	NPD5305	Approved
0.6483	Remote Similarity	NPD17	Approved
0.6483	Remote Similarity	NPD1778	Approved
0.6474	Remote Similarity	NPD2531	Phase 2
0.6474	Remote Similarity	NPD2438	Suspended
0.6474	Remote Similarity	NPD2796	Approved
0.6471	Remote Similarity	NPD4140	Approved
0.6471	Remote Similarity	NPD3787	Discontinued
0.6471	Remote Similarity	NPD4060	Phase 1
0.6471	Remote Similarity	NPD7871	Phase 2
0.6471	Remote Similarity	NPD5048	Discontinued
0.6471	Remote Similarity	NPD1240	Approved
0.6471	Remote Similarity	NPD7870	Phase 2
0.6467	Remote Similarity	NPD4965	Approved
0.6467	Remote Similarity	NPD4966	Approved
0.6467	Remote Similarity	NPD4967	Phase 2
0.6461	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD9545	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