NPASS Compound

Structure

NPC189651 OpenBabel07101719242D 21 23 0 0 1 0 0 0 0 0999 V2000 1.4253 -3.0984 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3554 1.6160 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 2.6228 -1.9010 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 1.6479 0.1235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4487 -0.1636 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6479 -2.1235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9487 0.7024 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 2 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 3.0567 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6228 -0.0990 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 -0.9706 0.4945 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 4.0567 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2463 0.6828 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2274 1.1637 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7796 -0.9067 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 8 1 0 0 0 0 3 10 1 0 0 0 0 4 8 2 0 0 0 0 4 12 1 0 0 0 0 5 10 1 0 0 0 0 5 11 1 0 0 0 0 6 13 2 0 0 0 0 6 14 1 0 0 0 0 7 9 1 0 0 0 0 7 20 1 0 0 0 0 8 11 1 0 0 0 0 9 2 1 1 0 0 0 9 15 1 0 0 0 0 10 16 1 1 0 0 0 11 14 2 0 0 0 0 12 13 1 0 0 0 0 12 17 2 0 0 0 0 13 18 1 0 0 0 0 14 21 1 0 0 0 0 15 16 1 1 0 0 0 15 19 1 0 0 0 0 16 20 1 6 0 0 0 16 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	292.13
Volume:	293.028
LogP:	1.565
LogD:	1.056
LogS:	-3.462
# Rotatable Bonds:	0
TPSA:	75.99
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.755
Synthetic Accessibility Score:	4.872
Fsp3:	0.562
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.652
MDCK Permeability:	6.812990704929689e-06
Pgp-inhibitor:	0.003
Pgp-substrate:	0.685
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.177

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.149
Plasma Protein Binding (PPB):	87.0361557006836%
Volume Distribution (VD):	0.671
Pgp-substrate:	7.463494777679443%

ADMET: Metabolism

CYP1A2-inhibitor:	0.106
CYP1A2-substrate:	0.814
CYP2C19-inhibitor:	0.023
CYP2C19-substrate:	0.806
CYP2C9-inhibitor:	0.016
CYP2C9-substrate:	0.346
CYP2D6-inhibitor:	0.013
CYP2D6-substrate:	0.322
CYP3A4-inhibitor:	0.031
CYP3A4-substrate:	0.268

ADMET: Excretion

Clearance (CL):	8.88
Half-life (T1/2):	0.436

ADMET: Toxicity

hERG Blockers:	0.03
Human Hepatotoxicity (H-HT):	0.936
Drug-inuced Liver Injury (DILI):	0.944
AMES Toxicity:	0.073
Rat Oral Acute Toxicity:	0.224
Maximum Recommended Daily Dose:	0.492
Skin Sensitization:	0.929
Carcinogencity:	0.159
Eye Corrosion:	0.003
Eye Irritation:	0.057
Respiratory Toxicity:	0.881

Download Data

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

Natural Product: NPC189651

Natural Product ID:	NPC189651
*Common Name:**	Malettinin B
IUPAC Name:	(2S,3R,3'R,4'R)-3',8-dihydroxy-3,4',5-trimethylspiro[3,4-dihydrocyclohepta[b]pyran-2,2'-oxolane]-7-one
Synonyms:
Standard InCHIKey:	PLRNIDHEWWILCN-HKBFDHSMSA-N
Standard InCHI:	InChI=1S/C16H20O5/c1-8-4-12(17)13(18)6-14-11(8)5-10(3)16(21-14)15(19)9(2)7-20-16/h4,6,9-10,15,19H,5,7H2,1-3H3,(H,17,18)/t9-,10-,15-,16+/m1/s1
SMILES:	C[C@@H]1CO[C@]2([C@@H]1O)Oc1cc(O)c(=O)cc(c1C[C@H]2C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL523562
PubChem CID:	11323788
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004150] Hydrocarbon derivatives [CHEMONTID:0001650] Tropones [CHEMONTID:0001674] Tropolones

*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
NPO33490	hypoxylon stromata nrrl 29110	Species	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15730245]

☑ 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	3

Activity Type	# Activity
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20	Organism	Candida albicans	Candida albicans	IZ	=	19.0	mm	PMID[509462]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IZ	=	24.0	mm	PMID[509462]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	IZ	=	26.0	mm	PMID[509462]

☑ 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 NPC189651 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	320
0.1-0.2	1222
0.2-0.3	3181
0.3-0.4	7695
0.4-0.5	10883
0.5-0.6	5127
0.6-0.7	7614
0.7-0.8	6575
0.8-0.85	73
0.85-0.9	5
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC475098
0.8065	Intermediate Similarity	NPC60765
0.8041	Intermediate Similarity	NPC288350
0.8041	Intermediate Similarity	NPC173329
0.8021	Intermediate Similarity	NPC256368
0.79	Intermediate Similarity	NPC197447
0.79	Intermediate Similarity	NPC169365
0.7835	Intermediate Similarity	NPC470521
0.7789	Intermediate Similarity	NPC133450
0.7732	Intermediate Similarity	NPC59646
0.7708	Intermediate Similarity	NPC177668
0.7629	Intermediate Similarity	NPC175842
0.7629	Intermediate Similarity	NPC32494
0.7629	Intermediate Similarity	NPC470520
0.76	Intermediate Similarity	NPC471490
0.7556	Intermediate Similarity	NPC326753
0.7551	Intermediate Similarity	NPC156553
0.7551	Intermediate Similarity	NPC469692
0.7551	Intermediate Similarity	NPC469645
0.7547	Intermediate Similarity	NPC133625
0.7526	Intermediate Similarity	NPC3436
0.7526	Intermediate Similarity	NPC327253
0.75	Intermediate Similarity	NPC474894
0.75	Intermediate Similarity	NPC473333
0.7475	Intermediate Similarity	NPC121825
0.7474	Intermediate Similarity	NPC311163
0.7449	Intermediate Similarity	NPC472010
0.7444	Intermediate Similarity	NPC315394
0.7429	Intermediate Similarity	NPC469852
0.7426	Intermediate Similarity	NPC2666
0.7423	Intermediate Similarity	NPC225283
0.7423	Intermediate Similarity	NPC64913
0.7423	Intermediate Similarity	NPC242877
0.7404	Intermediate Similarity	NPC472750
0.7404	Intermediate Similarity	NPC472747
0.7404	Intermediate Similarity	NPC197736
0.74	Intermediate Similarity	NPC471492
0.7383	Intermediate Similarity	NPC38154
0.7379	Intermediate Similarity	NPC219038
0.7374	Intermediate Similarity	NPC472196
0.7374	Intermediate Similarity	NPC320552
0.7374	Intermediate Similarity	NPC472195
0.7374	Intermediate Similarity	NPC238090
0.7368	Intermediate Similarity	NPC165162
0.7364	Intermediate Similarity	NPC82759
0.7358	Intermediate Similarity	NPC469853
0.7353	Intermediate Similarity	NPC203627
0.7347	Intermediate Similarity	NPC3952
0.734	Intermediate Similarity	NPC44261
0.7333	Intermediate Similarity	NPC472748
0.732	Intermediate Similarity	NPC260343
0.7312	Intermediate Similarity	NPC112868
0.7308	Intermediate Similarity	NPC291500
0.7308	Intermediate Similarity	NPC471599
0.7308	Intermediate Similarity	NPC189609
0.7308	Intermediate Similarity	NPC197835
0.7308	Intermediate Similarity	NPC140591
0.7308	Intermediate Similarity	NPC303653
0.73	Intermediate Similarity	NPC159698
0.7292	Intermediate Similarity	NPC472379
0.7282	Intermediate Similarity	NPC244878
0.7264	Intermediate Similarity	NPC472751
0.7264	Intermediate Similarity	NPC472749
0.7255	Intermediate Similarity	NPC120299
0.7255	Intermediate Similarity	NPC475332
0.7245	Intermediate Similarity	NPC210216
0.7238	Intermediate Similarity	NPC475871
0.7238	Intermediate Similarity	NPC475945
0.7216	Intermediate Similarity	NPC313658
0.7216	Intermediate Similarity	NPC45409
0.7216	Intermediate Similarity	NPC300779
0.7216	Intermediate Similarity	NPC316138
0.7212	Intermediate Similarity	NPC110443
0.7212	Intermediate Similarity	NPC20673
0.7212	Intermediate Similarity	NPC133907
0.7212	Intermediate Similarity	NPC46998
0.7212	Intermediate Similarity	NPC128733
0.7212	Intermediate Similarity	NPC185141
0.72	Intermediate Similarity	NPC471483
0.7188	Intermediate Similarity	NPC471494
0.7188	Intermediate Similarity	NPC471223
0.7188	Intermediate Similarity	NPC67081
0.7184	Intermediate Similarity	NPC151093
0.7184	Intermediate Similarity	NPC475653
0.7184	Intermediate Similarity	NPC187268
0.7172	Intermediate Similarity	NPC471569
0.7172	Intermediate Similarity	NPC129419
0.7158	Intermediate Similarity	NPC31019
0.7158	Intermediate Similarity	NPC263087
0.7158	Intermediate Similarity	NPC2379
0.7158	Intermediate Similarity	NPC106912
0.7158	Intermediate Similarity	NPC27314
0.7157	Intermediate Similarity	NPC255410
0.7143	Intermediate Similarity	NPC472378
0.7143	Intermediate Similarity	NPC106051
0.7143	Intermediate Similarity	NPC474747
0.7129	Intermediate Similarity	NPC477241
0.7128	Intermediate Similarity	NPC246621
0.7128	Intermediate Similarity	NPC281949
0.7128	Intermediate Similarity	NPC301477
0.7128	Intermediate Similarity	NPC25684
0.7113	Intermediate Similarity	NPC305475
0.7113	Intermediate Similarity	NPC475461
0.7113	Intermediate Similarity	NPC261721
0.7111	Intermediate Similarity	NPC107654
0.7103	Intermediate Similarity	NPC477125
0.7097	Intermediate Similarity	NPC139712
0.7097	Intermediate Similarity	NPC476701
0.7087	Intermediate Similarity	NPC266842
0.7083	Intermediate Similarity	NPC475706
0.7083	Intermediate Similarity	NPC266718
0.708	Intermediate Similarity	NPC471145
0.7075	Intermediate Similarity	NPC472755
0.7071	Intermediate Similarity	NPC307092
0.7071	Intermediate Similarity	NPC295448
0.7071	Intermediate Similarity	NPC268298
0.7065	Intermediate Similarity	NPC471225
0.7059	Intermediate Similarity	NPC471141
0.7059	Intermediate Similarity	NPC300710
0.7059	Intermediate Similarity	NPC13924
0.7053	Intermediate Similarity	NPC310450
0.7053	Intermediate Similarity	NPC474291
0.7053	Intermediate Similarity	NPC475046
0.7053	Intermediate Similarity	NPC474959
0.7053	Intermediate Similarity	NPC89555
0.7053	Intermediate Similarity	NPC11383
0.7048	Intermediate Similarity	NPC475157
0.7048	Intermediate Similarity	NPC472753
0.7048	Intermediate Similarity	NPC476270
0.7048	Intermediate Similarity	NPC471637
0.7048	Intermediate Similarity	NPC98859
0.7048	Intermediate Similarity	NPC164598
0.7048	Intermediate Similarity	NPC154132
0.7048	Intermediate Similarity	NPC2313
0.7048	Intermediate Similarity	NPC474339
0.7048	Intermediate Similarity	NPC57586
0.7048	Intermediate Similarity	NPC4637
0.7048	Intermediate Similarity	NPC475655
0.7048	Intermediate Similarity	NPC469851
0.7048	Intermediate Similarity	NPC474742
0.7041	Intermediate Similarity	NPC241054
0.7033	Intermediate Similarity	NPC315552
0.703	Intermediate Similarity	NPC475912
0.703	Intermediate Similarity	NPC273579
0.703	Intermediate Similarity	NPC288240
0.703	Intermediate Similarity	NPC475302
0.703	Intermediate Similarity	NPC162205
0.703	Intermediate Similarity	NPC295204
0.7027	Intermediate Similarity	NPC328074
0.7027	Intermediate Similarity	NPC470025
0.7027	Intermediate Similarity	NPC317460
0.7027	Intermediate Similarity	NPC321272
0.7019	Intermediate Similarity	NPC35717
0.7019	Intermediate Similarity	NPC161855
0.7019	Intermediate Similarity	NPC472015
0.7019	Intermediate Similarity	NPC65700
0.7019	Intermediate Similarity	NPC474440
0.701	Intermediate Similarity	NPC11804
0.701	Intermediate Similarity	NPC255307
0.7009	Intermediate Similarity	NPC474741
0.7009	Intermediate Similarity	NPC100487
0.7009	Intermediate Similarity	NPC264584
0.7	Intermediate Similarity	NPC202886
0.7	Intermediate Similarity	NPC316708
0.7	Intermediate Similarity	NPC472508
0.7	Intermediate Similarity	NPC475995
0.7	Intermediate Similarity	NPC316851
0.7	Intermediate Similarity	NPC469403
0.7	Intermediate Similarity	NPC474098
0.7	Intermediate Similarity	NPC475879
0.699	Remote Similarity	NPC172998
0.699	Remote Similarity	NPC299396
0.699	Remote Similarity	NPC473291
0.699	Remote Similarity	NPC301596
0.699	Remote Similarity	NPC306041
0.699	Remote Similarity	NPC16967
0.6981	Remote Similarity	NPC201191
0.6981	Remote Similarity	NPC472754
0.6981	Remote Similarity	NPC473596
0.6981	Remote Similarity	NPC149371
0.6979	Remote Similarity	NPC16488
0.6979	Remote Similarity	NPC284472
0.6979	Remote Similarity	NPC229799
0.6979	Remote Similarity	NPC475714
0.6979	Remote Similarity	NPC286770
0.6972	Remote Similarity	NPC472507
0.697	Remote Similarity	NPC472011
0.697	Remote Similarity	NPC473658
0.6964	Remote Similarity	NPC470027
0.6961	Remote Similarity	NPC191521
0.6961	Remote Similarity	NPC71589
0.6957	Remote Similarity	NPC301525
0.6952	Remote Similarity	NPC130792
0.6952	Remote Similarity	NPC227865
0.6947	Remote Similarity	NPC315731
0.6947	Remote Similarity	NPC184208
0.6947	Remote Similarity	NPC8538
0.6944	Remote Similarity	NPC82251
0.6944	Remote Similarity	NPC315070
0.6939	Remote Similarity	NPC208473

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 NPC189651 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	280
0.1-0.2	823
0.2-0.3	1826
0.3-0.4	2603
0.4-0.5	2059
0.5-0.6	1082
0.6-0.7	375
0.7-0.8	102
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7347	Intermediate Similarity	NPD7838	Discovery
0.7019	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD4225	Approved
0.6832	Remote Similarity	NPD46	Approved
0.6832	Remote Similarity	NPD6698	Approved
0.6786	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD7503	Approved
0.6667	Remote Similarity	NPD6686	Approved
0.6574	Remote Similarity	NPD5344	Discontinued
0.6571	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD6371	Approved
0.6481	Remote Similarity	NPD6648	Approved
0.6476	Remote Similarity	NPD5282	Discontinued
0.6354	Remote Similarity	NPD4756	Discovery
0.6333	Remote Similarity	NPD7299	Clinical (unspecified phase)
0.63	Remote Similarity	NPD6110	Phase 1
0.63	Remote Similarity	NPD7154	Phase 3
0.6286	Remote Similarity	NPD7983	Approved
0.6214	Remote Similarity	NPD7524	Approved
0.6207	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD6053	Discontinued
0.6154	Remote Similarity	NPD969	Suspended
0.6148	Remote Similarity	NPD8513	Phase 3
0.614	Remote Similarity	NPD6412	Phase 2
0.6117	Remote Similarity	NPD4249	Approved
0.6083	Remote Similarity	NPD7505	Discontinued
0.6083	Remote Similarity	NPD7115	Discovery
0.6078	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6058	Remote Similarity	NPD4251	Approved
0.6058	Remote Similarity	NPD4250	Approved
0.6055	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6044	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.604	Remote Similarity	NPD5209	Approved
0.6038	Remote Similarity	NPD5785	Approved
0.6033	Remote Similarity	NPD7327	Approved
0.6033	Remote Similarity	NPD7328	Approved
0.6019	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6016	Remote Similarity	NPD8517	Approved
0.6016	Remote Similarity	NPD8515	Approved
0.6016	Remote Similarity	NPD8033	Approved
0.6016	Remote Similarity	NPD8516	Approved
0.6	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5985	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.5984	Remote Similarity	NPD7516	Approved
0.598	Remote Similarity	NPD6695	Phase 3
0.5962	Remote Similarity	NPD5279	Phase 3
0.5935	Remote Similarity	NPD8377	Approved
0.5935	Remote Similarity	NPD6054	Approved
0.5935	Remote Similarity	NPD8294	Approved
0.5926	Remote Similarity	NPD5778	Approved
0.5926	Remote Similarity	NPD5779	Approved
0.592	Remote Similarity	NPD7829	Approved
0.592	Remote Similarity	NPD7830	Approved
0.5918	Remote Similarity	NPD6933	Approved
0.5909	Remote Similarity	NPD7839	Suspended
0.5902	Remote Similarity	NPD7641	Discontinued
0.5887	Remote Similarity	NPD8379	Approved
0.5887	Remote Similarity	NPD8296	Approved
0.5887	Remote Similarity	NPD6016	Approved
0.5887	Remote Similarity	NPD8335	Approved
0.5887	Remote Similarity	NPD8378	Approved
0.5887	Remote Similarity	NPD6015	Approved
0.5887	Remote Similarity	NPD8380	Approved
0.5882	Remote Similarity	NPD6882	Approved
0.5882	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5865	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.5865	Remote Similarity	NPD1696	Phase 3
0.5865	Remote Similarity	NPD1694	Approved
0.5865	Remote Similarity	NPD5363	Approved
0.5847	Remote Similarity	NPD2067	Discontinued
0.5842	Remote Similarity	NPD4820	Approved
0.5842	Remote Similarity	NPD4819	Approved
0.5842	Remote Similarity	NPD4821	Approved
0.5842	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.5842	Remote Similarity	NPD4695	Discontinued
0.5842	Remote Similarity	NPD4822	Approved
0.584	Remote Similarity	NPD6370	Approved
0.584	Remote Similarity	NPD5988	Approved
0.5833	Remote Similarity	NPD7637	Suspended
0.582	Remote Similarity	NPD7500	Approved
0.5806	Remote Similarity	NPD6059	Approved
0.5806	Remote Similarity	NPD3704	Approved
0.5804	Remote Similarity	NPD7638	Approved
0.58	Remote Similarity	NPD4271	Approved
0.58	Remote Similarity	NPD4268	Approved
0.5794	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5794	Remote Similarity	NPD6101	Approved
0.5794	Remote Similarity	NPD1695	Approved
0.5781	Remote Similarity	NPD8074	Phase 3
0.5778	Remote Similarity	NPD1145	Discontinued
0.576	Remote Similarity	NPD8444	Approved
0.5755	Remote Similarity	NPD7750	Discontinued
0.5752	Remote Similarity	NPD7640	Approved
0.5752	Remote Similarity	NPD7639	Approved
0.575	Remote Similarity	NPD8297	Approved
0.5748	Remote Similarity	NPD7492	Approved
0.5743	Remote Similarity	NPD6929	Approved
0.573	Remote Similarity	NPD69	Approved
0.573	Remote Similarity	NPD9119	Approved
0.5728	Remote Similarity	NPD6435	Approved
0.5726	Remote Similarity	NPD5697	Approved
0.5725	Remote Similarity	NPD7260	Phase 2
0.5714	Remote Similarity	NPD7623	Phase 3
0.5714	Remote Similarity	NPD6083	Phase 2
0.5714	Remote Similarity	NPD5125	Phase 3
0.5714	Remote Similarity	NPD6926	Approved
0.5714	Remote Similarity	NPD7624	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD6084	Phase 2
0.5714	Remote Similarity	NPD8080	Discontinued
0.5714	Remote Similarity	NPD5126	Approved
0.5714	Remote Similarity	NPD6924	Approved
0.5703	Remote Similarity	NPD7507	Approved
0.5703	Remote Similarity	NPD6616	Approved
0.5691	Remote Similarity	NPD6009	Approved
0.5688	Remote Similarity	NPD6411	Approved
0.5686	Remote Similarity	NPD6931	Approved
0.5686	Remote Similarity	NPD6930	Phase 2
0.5678	Remote Similarity	NPD6881	Approved
0.5678	Remote Similarity	NPD6899	Approved
0.5676	Remote Similarity	NPD5695	Phase 3
0.5673	Remote Similarity	NPD5362	Discontinued
0.5669	Remote Similarity	NPD7642	Approved
0.5659	Remote Similarity	NPD7078	Approved
0.5652	Remote Similarity	NPD5211	Phase 2
0.5652	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.5648	Remote Similarity	NPD4753	Phase 2
0.5641	Remote Similarity	NPD7128	Approved
0.5641	Remote Similarity	NPD6402	Approved
0.5641	Remote Similarity	NPD6675	Approved
0.5641	Remote Similarity	NPD5739	Approved
0.5641	Remote Similarity	NPD6640	Phase 3
0.563	Remote Similarity	NPD6014	Approved
0.563	Remote Similarity	NPD6013	Approved
0.563	Remote Similarity	NPD6012	Approved
0.563	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5618	Remote Similarity	NPD9118	Approved
0.5615	Remote Similarity	NPD7736	Approved
0.5614	Remote Similarity	NPD5286	Approved
0.5614	Remote Similarity	NPD4696	Approved
0.5614	Remote Similarity	NPD5285	Approved
0.5603	Remote Similarity	NPD6647	Phase 2

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