NPASS Compound

Structure

NPC293112 OpenBabel07101719122D 35 40 0 0 1 0 0 0 0 0999 V2000 -8.6257 1.3567 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2875 2.8430 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9179 0.3090 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 -7.0025 -1.2702 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6720 -1.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6665 -2.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 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 -3.4641 1.0000 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 -7.3386 0.1977 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6476 1.1488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9785 1.8920 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 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 -5.0733 -1.1691 0.0000 C 0 0 1 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 0.0000 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.3604 -0.0102 0.0000 C 0 0 2 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 2 0 0 0 0 0 0 0 0 0 -6.0003 1.6840 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 0.0000 C 0 0 2 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 -6.0514 -0.9612 0.0000 C 0 0 1 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 -2.5981 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.3312 2.4272 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.2593 -1.9394 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.6913 0.7330 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 13 1 0 0 0 0 2 14 1 0 0 0 0 3 25 1 0 0 0 0 4 26 1 0 0 0 0 5 27 1 0 0 0 0 6 7 1 0 0 0 0 6 15 1 0 0 0 0 7 17 1 0 0 0 0 8 9 2 0 0 0 0 8 18 1 0 0 0 0 9 19 1 0 0 0 0 10 11 1 0 0 0 0 10 16 1 0 0 0 0 11 25 1 0 0 0 0 12 13 1 0 0 0 0 12 20 1 0 0 0 0 13 14 2 0 0 0 0 14 24 1 0 0 0 0 15 21 1 0 0 0 0 15 25 1 6 0 0 0 16 21 1 0 0 0 0 16 26 1 6 0 0 0 17 25 1 6 0 0 0 17 27 1 0 0 0 0 18 26 1 0 0 0 0 18 29 2 0 0 0 0 19 28 1 6 0 0 0 19 30 1 0 0 0 0 20 27 1 1 0 0 0 20 34 1 0 0 0 0 21 22 1 0 0 0 0 22 23 1 0 0 0 0 22 31 1 0 0 0 0 23 28 1 0 0 0 0 23 35 1 0 0 0 0 24 32 2 0 0 0 0 24 34 1 0 0 0 0 26 28 1 0 0 0 0 27 33 1 0 0 0 0 28 35 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	486.26
Volume:	492.491
LogP:	2.952
LogD:	3.01
LogS:	-4.419
# Rotatable Bonds:	2
TPSA:	113.43
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	6
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.456
Synthetic Accessibility Score:	5.914
Fsp3:	0.821
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.963
MDCK Permeability:	2.958965524157975e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.98
Human Intestinal Absorption (HIA):	0.023
20% Bioavailability (F20%):	0.194
30% Bioavailability (F30%):	0.968

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.959
Plasma Protein Binding (PPB):	73.11394500732422%
Volume Distribution (VD):	0.996
Pgp-substrate:	18.63645362854004%

ADMET: Metabolism

CYP1A2-inhibitor:	0.03
CYP1A2-substrate:	0.602
CYP2C19-inhibitor:	0.082
CYP2C19-substrate:	0.79
CYP2C9-inhibitor:	0.073
CYP2C9-substrate:	0.033
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.133
CYP3A4-inhibitor:	0.52
CYP3A4-substrate:	0.508

ADMET: Excretion

Clearance (CL):	8.362
Half-life (T1/2):	0.874

ADMET: Toxicity

hERG Blockers:	0.327
Human Hepatotoxicity (H-HT):	0.219
Drug-inuced Liver Injury (DILI):	0.264
AMES Toxicity:	0.082
Rat Oral Acute Toxicity:	0.754
Maximum Recommended Daily Dose:	0.267
Skin Sensitization:	0.44
Carcinogencity:	0.779
Eye Corrosion:	0.013
Eye Irritation:	0.024
Respiratory Toxicity:	0.958

Download Data

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

Natural Product: NPC293112

Natural Product ID:	NPC293112
*Common Name:**	DMGHRMQAHYJTHX-YZYVTENCSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	DMGHRMQAHYJTHX-YZYVTENCSA-N
Standard InCHI:	InChI=1S/C28H38O7/c1-13-12-20(34-24(32)14(13)2)27(5,33)17-7-6-15-21-16(10-11-25(15,17)3)26(4)18(29)8-9-19(30)28(26)23(35-28)22(21)31/h8-9,15-17,19-23,30-31,33H,6-7,10-12H2,1-5H3/t15-,16-,17-,19-,20+,21-,22+,23+,25-,26-,27+,28+/m0/s1
SMILES:	CC1=C(C)C(=O)O[C@H](C1)[C@@](C)([C@H]1CC[C@H]2[C@H]3[C@H](CC[C@]12C)[C@@]1(C)C(=O)C=C[C@@H]([C@]21[C@@H]([C@@H]3O)O2)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL506683
PubChem CID:	23266160
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001125] Steroid lactones [CHEMONTID:0001560] Withanolides 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
NPO27252	Iochroma australe	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12027740]
NPO27252	Iochroma australe	Species	Solanaceae	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
Others	2

Activity Type	# Activity
Individual Protein	1
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT440	Individual Protein	Quinone oxidoreductase	Mus musculus	CD	=	0.51	uM	PMID[487906]
NPT27	Others	Unspecified		IC50	=	1270.0	nM	PMID[487906]
NPT2	Others	Unspecified		Ratio	=	2.5	n.a.	PMID[487906]

☑ 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 NPC293112 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	255
0.1-0.2	1415
0.2-0.3	3933
0.3-0.4	6786
0.4-0.5	11107
0.5-0.6	9204
0.6-0.7	6515
0.7-0.8	2890
0.8-0.85	416
0.85-0.9	121
0.9-0.95	39
0.95-1	16

Similarity Score	Similarity Level	Natural Product ID
0.9826	High Similarity	NPC469789
0.9826	High Similarity	NPC11895
0.9741	High Similarity	NPC172154
0.9741	High Similarity	NPC81736
0.9739	High Similarity	NPC170538
0.9658	High Similarity	NPC473635
0.9652	High Similarity	NPC67569
0.9573	High Similarity	NPC8369
0.9569	High Similarity	NPC470265
0.9569	High Similarity	NPC23786
0.9397	High Similarity	NPC268530
0.9397	High Similarity	NPC154491
0.9391	High Similarity	NPC709
0.9391	High Similarity	NPC50774
0.9316	High Similarity	NPC159456
0.9316	High Similarity	NPC4021
0.9304	High Similarity	NPC140055
0.9304	High Similarity	NPC286528
0.9304	High Similarity	NPC20302
0.9304	High Similarity	NPC167606
0.9244	High Similarity	NPC8374
0.9237	High Similarity	NPC269642
0.9231	High Similarity	NPC251226
0.9231	High Similarity	NPC474370
0.9153	High Similarity	NPC46570
0.9145	High Similarity	NPC475041
0.9145	High Similarity	NPC264954
0.9138	High Similarity	NPC183580
0.9138	High Similarity	NPC312824
0.9138	High Similarity	NPC469684
0.9138	High Similarity	NPC470492
0.9138	High Similarity	NPC470493
0.913	High Similarity	NPC67259
0.913	High Similarity	NPC147912
0.9098	High Similarity	NPC231529
0.9098	High Similarity	NPC473593
0.9076	High Similarity	NPC88326
0.9076	High Similarity	NPC107493
0.9076	High Similarity	NPC153700
0.9068	High Similarity	NPC476961
0.9052	High Similarity	NPC270929
0.9043	High Similarity	NPC122056
0.9008	High Similarity	NPC120994
0.9008	High Similarity	NPC203702
0.8983	High Similarity	NPC42673
0.8983	High Similarity	NPC476960
0.8983	High Similarity	NPC475520
0.8983	High Similarity	NPC230513
0.8983	High Similarity	NPC61520
0.8974	High Similarity	NPC55296
0.8966	High Similarity	NPC284915
0.8952	High Similarity	NPC231240
0.8934	High Similarity	NPC287423
0.8934	High Similarity	NPC473253
0.8926	High Similarity	NPC469790
0.8898	High Similarity	NPC186525
0.8898	High Similarity	NPC284707
0.8898	High Similarity	NPC329736
0.888	High Similarity	NPC316915
0.8862	High Similarity	NPC473620
0.8843	High Similarity	NPC120724
0.8843	High Similarity	NPC473979
0.8843	High Similarity	NPC204812
0.8824	High Similarity	NPC473274
0.8814	High Similarity	NPC470959
0.8814	High Similarity	NPC98249
0.8814	High Similarity	NPC53396
0.8814	High Similarity	NPC476965
0.8814	High Similarity	NPC58662
0.8803	High Similarity	NPC238667
0.8793	High Similarity	NPC269530
0.8793	High Similarity	NPC236217
0.879	High Similarity	NPC470880
0.879	High Similarity	NPC476966
0.878	High Similarity	NPC470882
0.877	High Similarity	NPC3381
0.877	High Similarity	NPC32868
0.877	High Similarity	NPC241456
0.877	High Similarity	NPC470494
0.875	High Similarity	NPC476962
0.875	High Similarity	NPC79579
0.8739	High Similarity	NPC153440
0.8739	High Similarity	NPC473720
0.8729	High Similarity	NPC176840
0.8729	High Similarity	NPC190286
0.8729	High Similarity	NPC64318
0.8718	High Similarity	NPC25909
0.8718	High Similarity	NPC317210
0.8707	High Similarity	NPC469656
0.8707	High Similarity	NPC469655
0.8707	High Similarity	NPC474846
0.8707	High Similarity	NPC474229
0.8689	High Similarity	NPC67251
0.8678	High Similarity	NPC473256
0.8678	High Similarity	NPC470878
0.8678	High Similarity	NPC310511
0.8667	High Similarity	NPC77689
0.8667	High Similarity	NPC473636
0.8667	High Similarity	NPC473203
0.8667	High Similarity	NPC5292
0.8655	High Similarity	NPC474518
0.8655	High Similarity	NPC134430
0.8655	High Similarity	NPC243065
0.8644	High Similarity	NPC474181
0.8629	High Similarity	NPC42399
0.8629	High Similarity	NPC473265
0.8621	High Similarity	NPC472215
0.8621	High Similarity	NPC37116
0.8621	High Similarity	NPC253906
0.8621	High Similarity	NPC472214
0.8618	High Similarity	NPC470922
0.8618	High Similarity	NPC24651
0.8618	High Similarity	NPC476729
0.8595	High Similarity	NPC474585
0.8583	High Similarity	NPC108581
0.8583	High Similarity	NPC478206
0.8583	High Similarity	NPC251310
0.8583	High Similarity	NPC478205
0.8571	High Similarity	NPC470075
0.856	High Similarity	NPC245094
0.8559	High Similarity	NPC962
0.8559	High Similarity	NPC250109
0.8547	High Similarity	NPC474315
0.8537	High Similarity	NPC265557
0.8537	High Similarity	NPC18945
0.8537	High Similarity	NPC105926
0.8537	High Similarity	NPC91693
0.8534	High Similarity	NPC469370
0.8534	High Similarity	NPC284828
0.8534	High Similarity	NPC5475
0.8534	High Similarity	NPC173905
0.8534	High Similarity	NPC472216
0.8512	High Similarity	NPC270850
0.8512	High Similarity	NPC473270
0.8512	High Similarity	NPC211093
0.8512	High Similarity	NPC305260
0.8512	High Similarity	NPC473839
0.8512	High Similarity	NPC472667
0.8504	High Similarity	NPC471855
0.85	High Similarity	NPC13713
0.85	High Similarity	NPC478204
0.85	High Similarity	NPC475809
0.85	High Similarity	NPC473968
0.85	High Similarity	NPC284068
0.8487	Intermediate Similarity	NPC470953
0.8487	Intermediate Similarity	NPC243354
0.8487	Intermediate Similarity	NPC117712
0.8475	Intermediate Similarity	NPC472002
0.8475	Intermediate Similarity	NPC90952
0.8475	Intermediate Similarity	NPC191620
0.8475	Intermediate Similarity	NPC476163
0.8475	Intermediate Similarity	NPC277769
0.8468	Intermediate Similarity	NPC473709
0.8468	Intermediate Similarity	NPC473919
0.8468	Intermediate Similarity	NPC318135
0.8468	Intermediate Similarity	NPC473255
0.8462	Intermediate Similarity	NPC29133
0.8462	Intermediate Similarity	NPC76084
0.8455	Intermediate Similarity	NPC312833
0.8455	Intermediate Similarity	NPC222688
0.8448	Intermediate Similarity	NPC472218
0.8448	Intermediate Similarity	NPC472219
0.8448	Intermediate Similarity	NPC472217
0.8443	Intermediate Similarity	NPC475885
0.843	Intermediate Similarity	NPC146280
0.843	Intermediate Similarity	NPC311554
0.843	Intermediate Similarity	NPC124676
0.843	Intermediate Similarity	NPC257457
0.8425	Intermediate Similarity	NPC173347
0.8417	Intermediate Similarity	NPC179626
0.8417	Intermediate Similarity	NPC266728
0.8417	Intermediate Similarity	NPC154363
0.8417	Intermediate Similarity	NPC471127
0.8417	Intermediate Similarity	NPC49492
0.8417	Intermediate Similarity	NPC234858
0.8413	Intermediate Similarity	NPC311534
0.8403	Intermediate Similarity	NPC194273
0.8403	Intermediate Similarity	NPC477126
0.84	Intermediate Similarity	NPC225049
0.839	Intermediate Similarity	NPC471243
0.839	Intermediate Similarity	NPC470961
0.839	Intermediate Similarity	NPC317107
0.839	Intermediate Similarity	NPC470076
0.839	Intermediate Similarity	NPC470960
0.8387	Intermediate Similarity	NPC472399
0.8387	Intermediate Similarity	NPC473802
0.8374	Intermediate Similarity	NPC477046
0.8374	Intermediate Similarity	NPC102822
0.8374	Intermediate Similarity	NPC470779
0.8372	Intermediate Similarity	NPC476823
0.8362	Intermediate Similarity	NPC91034
0.8362	Intermediate Similarity	NPC187435
0.8362	Intermediate Similarity	NPC67321
0.8362	Intermediate Similarity	NPC180744
0.8361	Intermediate Similarity	NPC236918
0.8361	Intermediate Similarity	NPC156745
0.8361	Intermediate Similarity	NPC475775
0.8361	Intermediate Similarity	NPC476529
0.8359	Intermediate Similarity	NPC476193
0.8347	Intermediate Similarity	NPC287343

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 NPC293112 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	231
0.1-0.2	1568
0.2-0.3	3574
0.3-0.4	2425
0.4-0.5	744
0.5-0.6	346
0.6-0.7	162
0.7-0.8	98
0.8-0.85	1
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9304	High Similarity	NPD7115	Discovery
0.8145	Intermediate Similarity	NPD6319	Approved
0.8067	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.8062	Intermediate Similarity	NPD7319	Approved
0.7983	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7951	Intermediate Similarity	NPD4632	Approved
0.7891	Intermediate Similarity	NPD7492	Approved
0.7869	Intermediate Similarity	NPD8297	Approved
0.7857	Intermediate Similarity	NPD6054	Approved
0.7851	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7846	Intermediate Similarity	NPD7736	Approved
0.7833	Intermediate Similarity	NPD6881	Approved
0.7833	Intermediate Similarity	NPD6899	Approved
0.7829	Intermediate Similarity	NPD7507	Approved
0.7829	Intermediate Similarity	NPD6616	Approved
0.7815	Intermediate Similarity	NPD6008	Approved
0.7787	Intermediate Similarity	NPD6650	Approved
0.7787	Intermediate Similarity	NPD6649	Approved
0.7769	Intermediate Similarity	NPD7078	Approved
0.7759	Intermediate Similarity	NPD4225	Approved
0.775	Intermediate Similarity	NPD5697	Approved
0.7734	Intermediate Similarity	NPD6370	Approved
0.7705	Intermediate Similarity	NPD4634	Approved
0.7705	Intermediate Similarity	NPD7290	Approved
0.7705	Intermediate Similarity	NPD7102	Approved
0.7705	Intermediate Similarity	NPD6883	Approved
0.7692	Intermediate Similarity	NPD7639	Approved
0.7692	Intermediate Similarity	NPD7640	Approved
0.7674	Intermediate Similarity	NPD7604	Phase 2
0.7667	Intermediate Similarity	NPD6402	Approved
0.7667	Intermediate Similarity	NPD7128	Approved
0.7667	Intermediate Similarity	NPD6675	Approved
0.7667	Intermediate Similarity	NPD5739	Approved
0.7656	Intermediate Similarity	NPD6016	Approved
0.7656	Intermediate Similarity	NPD6015	Approved
0.7642	Intermediate Similarity	NPD6617	Approved
0.7642	Intermediate Similarity	NPD6869	Approved
0.7642	Intermediate Similarity	NPD8130	Phase 1
0.7642	Intermediate Similarity	NPD6847	Approved
0.7627	Intermediate Similarity	NPD5344	Discontinued
0.7623	Intermediate Similarity	NPD6014	Approved
0.7623	Intermediate Similarity	NPD6373	Approved
0.7623	Intermediate Similarity	NPD6013	Approved
0.7623	Intermediate Similarity	NPD6372	Approved
0.7623	Intermediate Similarity	NPD6012	Approved
0.7619	Intermediate Similarity	NPD6009	Approved
0.7607	Intermediate Similarity	NPD7638	Approved
0.7603	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD5988	Approved
0.7581	Intermediate Similarity	NPD6882	Approved
0.7578	Intermediate Similarity	NPD6059	Approved
0.7563	Intermediate Similarity	NPD5211	Phase 2
0.7561	Intermediate Similarity	NPD6371	Approved
0.7541	Intermediate Similarity	NPD7320	Approved
0.7541	Intermediate Similarity	NPD6011	Approved
0.7519	Intermediate Similarity	NPD5983	Phase 2
0.7519	Intermediate Similarity	NPD8513	Phase 3
0.7519	Intermediate Similarity	NPD7503	Approved
0.75	Intermediate Similarity	NPD7516	Approved
0.75	Intermediate Similarity	NPD8293	Discontinued
0.7459	Intermediate Similarity	NPD5701	Approved
0.744	Intermediate Similarity	NPD6053	Discontinued
0.7438	Intermediate Similarity	NPD5141	Approved
0.7424	Intermediate Similarity	NPD6336	Discontinued
0.7422	Intermediate Similarity	NPD7328	Approved
0.7422	Intermediate Similarity	NPD7327	Approved
0.7405	Intermediate Similarity	NPD8328	Phase 3
0.7398	Intermediate Similarity	NPD6686	Approved
0.7395	Intermediate Similarity	NPD4696	Approved
0.7395	Intermediate Similarity	NPD5285	Approved
0.7395	Intermediate Similarity	NPD5286	Approved
0.7391	Intermediate Similarity	NPD6079	Approved
0.7385	Intermediate Similarity	NPD8517	Approved
0.7385	Intermediate Similarity	NPD8515	Approved
0.7385	Intermediate Similarity	NPD8516	Approved
0.7328	Intermediate Similarity	NPD6399	Phase 3
0.7317	Intermediate Similarity	NPD6412	Phase 2
0.7273	Intermediate Similarity	NPD4633	Approved
0.7273	Intermediate Similarity	NPD5225	Approved
0.7273	Intermediate Similarity	NPD5226	Approved
0.7273	Intermediate Similarity	NPD5224	Approved
0.7252	Intermediate Similarity	NPD8379	Approved
0.7252	Intermediate Similarity	NPD8033	Approved
0.7252	Intermediate Similarity	NPD8296	Approved
0.7252	Intermediate Similarity	NPD6921	Approved
0.7252	Intermediate Similarity	NPD8380	Approved
0.7252	Intermediate Similarity	NPD8335	Approved
0.7252	Intermediate Similarity	NPD8378	Approved
0.725	Intermediate Similarity	NPD6648	Approved
0.7231	Intermediate Similarity	NPD7101	Approved
0.7231	Intermediate Similarity	NPD7100	Approved
0.7227	Intermediate Similarity	NPD4755	Approved
0.7222	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7217	Intermediate Similarity	NPD5328	Approved
0.7213	Intermediate Similarity	NPD5175	Approved
0.7213	Intermediate Similarity	NPD5174	Approved
0.719	Intermediate Similarity	NPD5223	Approved
0.7176	Intermediate Similarity	NPD8377	Approved
0.7176	Intermediate Similarity	NPD8294	Approved
0.7154	Intermediate Similarity	NPD6335	Approved
0.7143	Intermediate Similarity	NPD5222	Approved
0.7143	Intermediate Similarity	NPD5221	Approved
0.7143	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD6274	Approved
0.7131	Intermediate Similarity	NPD7632	Discontinued
0.7107	Intermediate Similarity	NPD4700	Approved
0.7094	Intermediate Similarity	NPD7637	Suspended
0.7083	Intermediate Similarity	NPD6084	Phase 2
0.7083	Intermediate Similarity	NPD6083	Phase 2
0.7083	Intermediate Similarity	NPD7902	Approved
0.7083	Intermediate Similarity	NPD5173	Approved
0.7077	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD6317	Approved
0.7063	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6033	Approved
0.7034	Intermediate Similarity	NPD5779	Approved
0.7034	Intermediate Similarity	NPD5778	Approved
0.7029	Intermediate Similarity	NPD7260	Phase 2
0.7023	Intermediate Similarity	NPD6314	Approved
0.7023	Intermediate Similarity	NPD6313	Approved
0.7009	Intermediate Similarity	NPD6698	Approved
0.7009	Intermediate Similarity	NPD5785	Approved
0.7009	Intermediate Similarity	NPD46	Approved
0.7	Intermediate Similarity	NPD4697	Phase 3
0.7	Intermediate Similarity	NPD6868	Approved
0.6992	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD8074	Phase 3
0.6984	Remote Similarity	NPD4730	Approved
0.6984	Remote Similarity	NPD4729	Approved
0.6977	Remote Similarity	NPD8133	Approved
0.6975	Remote Similarity	NPD7748	Approved
0.6957	Remote Similarity	NPD3618	Phase 1
0.6949	Remote Similarity	NPD7515	Phase 2
0.6917	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD3573	Approved
0.6891	Remote Similarity	NPD4202	Approved
0.6885	Remote Similarity	NPD5696	Approved
0.6875	Remote Similarity	NPD5250	Approved
0.6875	Remote Similarity	NPD5249	Phase 3
0.6875	Remote Similarity	NPD5248	Approved
0.6875	Remote Similarity	NPD5247	Approved
0.6875	Remote Similarity	NPD5251	Approved
0.6866	Remote Similarity	NPD6909	Approved
0.6866	Remote Similarity	NPD6908	Approved
0.685	Remote Similarity	NPD5128	Approved
0.6833	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD7900	Approved
0.6825	Remote Similarity	NPD4767	Approved
0.6825	Remote Similarity	NPD4768	Approved
0.6822	Remote Similarity	NPD5216	Approved
0.6822	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD5217	Approved
0.6822	Remote Similarity	NPD5215	Approved
0.681	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD8034	Phase 2
0.6807	Remote Similarity	NPD8035	Phase 2
0.6807	Remote Similarity	NPD7983	Approved
0.6807	Remote Similarity	NPD6411	Approved
0.68	Remote Similarity	NPD4754	Approved
0.6783	Remote Similarity	NPD4786	Approved
0.6777	Remote Similarity	NPD4629	Approved
0.6777	Remote Similarity	NPD5210	Approved
0.6777	Remote Similarity	NPD5695	Phase 3
0.6752	Remote Similarity	NPD7524	Approved
0.6744	Remote Similarity	NPD5169	Approved
0.6744	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD5135	Approved
0.6724	Remote Similarity	NPD1694	Approved
0.6723	Remote Similarity	NPD7838	Discovery
0.6695	Remote Similarity	NPD5737	Approved
0.6695	Remote Similarity	NPD6672	Approved
0.6695	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD5127	Approved
0.6667	Remote Similarity	NPD7521	Approved
0.6667	Remote Similarity	NPD5284	Approved
0.6667	Remote Similarity	NPD7146	Approved
0.6667	Remote Similarity	NPD5330	Approved
0.6667	Remote Similarity	NPD7334	Approved
0.6667	Remote Similarity	NPD6684	Approved
0.6667	Remote Similarity	NPD5693	Phase 1
0.6667	Remote Similarity	NPD5281	Approved
0.6667	Remote Similarity	NPD6409	Approved
0.6639	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD4753	Phase 2
0.6639	Remote Similarity	NPD6101	Approved
0.6623	Remote Similarity	NPD7236	Approved
0.6621	Remote Similarity	NPD6333	Approved
0.6621	Remote Similarity	NPD6334	Approved
0.662	Remote Similarity	NPD6845	Suspended
0.6609	Remote Similarity	NPD3667	Approved
0.6596	Remote Similarity	NPD5956	Approved
0.6593	Remote Similarity	NPD4522	Approved
0.6589	Remote Similarity	NPD5168	Approved
0.6581	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD5363	Approved
0.6557	Remote Similarity	NPD6001	Approved
0.6555	Remote Similarity	NPD6903	Approved
0.6541	Remote Similarity	NPD5167	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