NPASS Compound

Structure

NPC193920 OpenBabel07101719242D 26 30 0 0 1 0 0 0 0 0999 V2000 -3.1631 -0.9757 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4311 2.0243 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1631 0.0243 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2971 1.5243 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2971 -1.4757 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5651 1.5243 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8084 -2.2687 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0576 -1.7687 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5405 0.7313 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2971 0.5243 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6744 -1.7687 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5405 -0.2687 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6744 1.2313 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.4311 -0.9757 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5651 0.5243 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4311 0.0243 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6744 -0.7687 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8084 -0.2687 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8084 0.7313 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0576 -0.7687 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5405 -2.2687 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4065 -0.7687 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6744 2.2313 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0576 1.2313 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6945 -1.2029 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 3 2 0 0 0 0 1 5 1 0 0 0 0 2 4 2 0 0 0 0 2 6 1 0 0 0 0 3 10 1 0 0 0 0 4 10 1 0 0 0 0 5 14 2 0 0 0 0 6 15 2 0 0 0 0 7 8 2 0 0 0 0 7 11 1 0 0 0 0 8 20 1 0 0 0 0 9 12 1 0 0 0 0 9 13 1 0 0 0 0 10 16 2 0 0 0 0 11 17 1 0 0 0 0 11 21 1 1 0 0 0 12 17 1 0 0 0 0 12 22 1 6 0 0 0 13 19 1 0 0 0 0 13 23 1 1 0 0 0 14 16 1 0 0 0 0 14 25 1 0 0 0 0 15 16 1 0 0 0 0 15 26 1 0 0 0 0 17 18 1 0 0 0 0 18 19 1 0 0 0 0 18 20 1 0 0 0 0 19 24 1 0 0 0 0 20 25 1 0 0 0 0 20 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	356.13
Volume:	348.616
LogP:	1.607
LogD:	1.994
LogS:	-3.339
# Rotatable Bonds:	0
TPSA:	99.38
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.525
Synthetic Accessibility Score:	5.006
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:	-5.361
MDCK Permeability:	3.859479693346657e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.025
Human Intestinal Absorption (HIA):	0.023
20% Bioavailability (F20%):	0.009
30% Bioavailability (F30%):	0.615

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.685
Plasma Protein Binding (PPB):	92.65409088134766%
Volume Distribution (VD):	0.751
Pgp-substrate:	9.718270301818848%

ADMET: Metabolism

CYP1A2-inhibitor:	0.186
CYP1A2-substrate:	0.102
CYP2C19-inhibitor:	0.071
CYP2C19-substrate:	0.368
CYP2C9-inhibitor:	0.095
CYP2C9-substrate:	0.765
CYP2D6-inhibitor:	0.046
CYP2D6-substrate:	0.171
CYP3A4-inhibitor:	0.059
CYP3A4-substrate:	0.127

ADMET: Excretion

Clearance (CL):	9.568
Half-life (T1/2):	0.696

ADMET: Toxicity

hERG Blockers:	0.049
Human Hepatotoxicity (H-HT):	0.87
Drug-inuced Liver Injury (DILI):	0.045
AMES Toxicity:	0.11
Rat Oral Acute Toxicity:	0.705
Maximum Recommended Daily Dose:	0.057
Skin Sensitization:	0.153
Carcinogencity:	0.825
Eye Corrosion:	0.003
Eye Irritation:	0.028
Respiratory Toxicity:	0.969

Download Data

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

Natural Product: NPC193920

Natural Product ID:	NPC193920
*Common Name:**	Decaspirone H
IUPAC Name:	n.a.
Synonyms:	Decaspirone H
Standard InCHIKey:	CBSLQPGXNHOHQN-HTUUWXQOSA-N
Standard InCHI:	InChI=1S/C20H20O6/c21-11-7-8-20(18-17(11)12(22)9-13(23)19(18)24)25-14-5-1-3-10-4-2-6-15(26-20)16(10)14/h1-8,11-13,17-19,21-24H,9H2/t11-,12-,13-,17+,18-,19+/m0/s1
SMILES:	O[C@H]1C[C@H](O)[C@@H]2[C@@H]([C@@H]1O)C1(C=C[C@@H]2O)Oc2cccc3c2c(O1)ccc3
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL465557
PubChem CID:	16099381
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000023] Naphthalenes

*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
NPO33005	helicoma viridis	Species	Tubeufiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17190440]

☑ 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
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	IZ	=	8.0	mm	PMID[483661]

☑ 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 NPC193920 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	441
0.1-0.2	1535
0.2-0.3	3883
0.3-0.4	9878
0.4-0.5	8960
0.5-0.6	4506
0.6-0.7	9298
0.7-0.8	3744
0.8-0.85	421
0.85-0.9	21
0.9-0.95	9
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9493	High Similarity	NPC472154
0.9424	High Similarity	NPC288531
0.9338	High Similarity	NPC472151
0.9281	High Similarity	NPC472155
0.9281	High Similarity	NPC151704
0.9248	High Similarity	NPC284232
0.9214	High Similarity	NPC173630
0.9214	High Similarity	NPC271076
0.9111	High Similarity	NPC138940
0.9078	High Similarity	NPC23807
0.8913	High Similarity	NPC92932
0.8675	High Similarity	NPC472156
0.8671	High Similarity	NPC197461
0.8671	High Similarity	NPC472451
0.8649	High Similarity	NPC21902
0.8649	High Similarity	NPC233467
0.8531	High Similarity	NPC178054
0.8523	High Similarity	NPC469944
0.8523	High Similarity	NPC272552
0.8523	High Similarity	NPC226108
0.8523	High Similarity	NPC322899
0.8523	High Similarity	NPC46283
0.8523	High Similarity	NPC134911
0.8523	High Similarity	NPC44192
0.8511	High Similarity	NPC234952
0.8503	High Similarity	NPC175976
0.8497	Intermediate Similarity	NPC100936
0.8497	Intermediate Similarity	NPC1253
0.8493	Intermediate Similarity	NPC99515
0.8493	Intermediate Similarity	NPC102280
0.8493	Intermediate Similarity	NPC97662
0.8493	Intermediate Similarity	NPC248053
0.8493	Intermediate Similarity	NPC190714
0.8493	Intermediate Similarity	NPC155564
0.8483	Intermediate Similarity	NPC76176
0.8483	Intermediate Similarity	NPC138227
0.8483	Intermediate Similarity	NPC168579
0.8483	Intermediate Similarity	NPC469313
0.8483	Intermediate Similarity	NPC257404
0.8467	Intermediate Similarity	NPC20050
0.8467	Intermediate Similarity	NPC78809
0.8467	Intermediate Similarity	NPC306267
0.8451	Intermediate Similarity	NPC134260
0.8435	Intermediate Similarity	NPC473480
0.8435	Intermediate Similarity	NPC15538
0.8417	Intermediate Similarity	NPC121376
0.8414	Intermediate Similarity	NPC37793
0.8414	Intermediate Similarity	NPC163508
0.8414	Intermediate Similarity	NPC252169
0.8414	Intermediate Similarity	NPC173203
0.8414	Intermediate Similarity	NPC473044
0.8406	Intermediate Similarity	NPC218003
0.8403	Intermediate Similarity	NPC108674
0.8403	Intermediate Similarity	NPC210192
0.8403	Intermediate Similarity	NPC471389
0.84	Intermediate Similarity	NPC474442
0.84	Intermediate Similarity	NPC59692
0.8392	Intermediate Similarity	NPC471388
0.8392	Intermediate Similarity	NPC32630
0.8389	Intermediate Similarity	NPC225815
0.8389	Intermediate Similarity	NPC469706
0.8389	Intermediate Similarity	NPC214326
0.8389	Intermediate Similarity	NPC9933
0.8389	Intermediate Similarity	NPC469707
0.8389	Intermediate Similarity	NPC185955
0.8389	Intermediate Similarity	NPC145979
0.8389	Intermediate Similarity	NPC260781
0.8389	Intermediate Similarity	NPC238140
0.8389	Intermediate Similarity	NPC218041
0.8389	Intermediate Similarity	NPC182368
0.838	Intermediate Similarity	NPC472800
0.838	Intermediate Similarity	NPC475628
0.8378	Intermediate Similarity	NPC280945
0.8369	Intermediate Similarity	NPC188555
0.8369	Intermediate Similarity	NPC473107
0.8369	Intermediate Similarity	NPC130496
0.8367	Intermediate Similarity	NPC125755
0.8357	Intermediate Similarity	NPC165686
0.8357	Intermediate Similarity	NPC303422
0.8357	Intermediate Similarity	NPC85799
0.8357	Intermediate Similarity	NPC26080
0.8356	Intermediate Similarity	NPC15659
0.8356	Intermediate Similarity	NPC473045
0.8356	Intermediate Similarity	NPC304894
0.8356	Intermediate Similarity	NPC25292
0.8356	Intermediate Similarity	NPC473108
0.8345	Intermediate Similarity	NPC472353
0.8345	Intermediate Similarity	NPC60249
0.8345	Intermediate Similarity	NPC475084
0.8344	Intermediate Similarity	NPC472150
0.8333	Intermediate Similarity	NPC182509
0.8333	Intermediate Similarity	NPC174787
0.8333	Intermediate Similarity	NPC213607
0.8333	Intermediate Similarity	NPC109240
0.8323	Intermediate Similarity	NPC472153
0.8322	Intermediate Similarity	NPC262328
0.8322	Intermediate Similarity	NPC44452
0.8322	Intermediate Similarity	NPC87777
0.8312	Intermediate Similarity	NPC193749
0.8311	Intermediate Similarity	NPC206579
0.8311	Intermediate Similarity	NPC204770
0.8311	Intermediate Similarity	NPC108811
0.8311	Intermediate Similarity	NPC202742
0.8311	Intermediate Similarity	NPC263940
0.8311	Intermediate Similarity	NPC170103
0.8311	Intermediate Similarity	NPC236202
0.8311	Intermediate Similarity	NPC82917
0.8311	Intermediate Similarity	NPC58190
0.8311	Intermediate Similarity	NPC262911
0.8311	Intermediate Similarity	NPC294558
0.8311	Intermediate Similarity	NPC227902
0.8311	Intermediate Similarity	NPC18185
0.8311	Intermediate Similarity	NPC11800
0.8311	Intermediate Similarity	NPC70409
0.831	Intermediate Similarity	NPC15109
0.831	Intermediate Similarity	NPC61946
0.831	Intermediate Similarity	NPC238243
0.831	Intermediate Similarity	NPC79957
0.831	Intermediate Similarity	NPC11727
0.831	Intermediate Similarity	NPC164787
0.8299	Intermediate Similarity	NPC11422
0.8299	Intermediate Similarity	NPC472457
0.8299	Intermediate Similarity	NPC277867
0.8299	Intermediate Similarity	NPC307466
0.8299	Intermediate Similarity	NPC475096
0.8299	Intermediate Similarity	NPC178014
0.8299	Intermediate Similarity	NPC42716
0.8299	Intermediate Similarity	NPC474749
0.8299	Intermediate Similarity	NPC161700
0.8298	Intermediate Similarity	NPC115022
0.8298	Intermediate Similarity	NPC11060
0.8298	Intermediate Similarity	NPC294166
0.8298	Intermediate Similarity	NPC263064
0.8298	Intermediate Similarity	NPC177712
0.8298	Intermediate Similarity	NPC24913
0.8288	Intermediate Similarity	NPC133585
0.8288	Intermediate Similarity	NPC81638
0.8286	Intermediate Similarity	NPC475067
0.8278	Intermediate Similarity	NPC325860
0.8276	Intermediate Similarity	NPC100482
0.8276	Intermediate Similarity	NPC76871
0.8276	Intermediate Similarity	NPC265075
0.8276	Intermediate Similarity	NPC277331
0.8276	Intermediate Similarity	NPC469661
0.8273	Intermediate Similarity	NPC97326
0.8267	Intermediate Similarity	NPC195561
0.8267	Intermediate Similarity	NPC158784
0.8264	Intermediate Similarity	NPC127218
0.8264	Intermediate Similarity	NPC245207
0.8264	Intermediate Similarity	NPC292487
0.8264	Intermediate Similarity	NPC319647
0.8264	Intermediate Similarity	NPC25966
0.8255	Intermediate Similarity	NPC270751
0.8255	Intermediate Similarity	NPC212142
0.8255	Intermediate Similarity	NPC329836
0.8255	Intermediate Similarity	NPC227516
0.8255	Intermediate Similarity	NPC301961
0.8255	Intermediate Similarity	NPC20757
0.8255	Intermediate Similarity	NPC166584
0.8252	Intermediate Similarity	NPC302701
0.8252	Intermediate Similarity	NPC172818
0.8252	Intermediate Similarity	NPC203230
0.8252	Intermediate Similarity	NPC16435
0.8252	Intermediate Similarity	NPC269091
0.8252	Intermediate Similarity	NPC248727
0.8252	Intermediate Similarity	NPC40664
0.8252	Intermediate Similarity	NPC270456
0.8252	Intermediate Similarity	NPC197723
0.8252	Intermediate Similarity	NPC165482
0.8252	Intermediate Similarity	NPC306441
0.8252	Intermediate Similarity	NPC173660
0.8252	Intermediate Similarity	NPC3293
0.8252	Intermediate Similarity	NPC104167
0.8252	Intermediate Similarity	NPC25695
0.8252	Intermediate Similarity	NPC265433
0.8252	Intermediate Similarity	NPC242028
0.8252	Intermediate Similarity	NPC162659
0.8252	Intermediate Similarity	NPC138350
0.8247	Intermediate Similarity	NPC4809
0.8247	Intermediate Similarity	NPC147743
0.8247	Intermediate Similarity	NPC73517
0.8243	Intermediate Similarity	NPC96576
0.8243	Intermediate Similarity	NPC226540
0.8243	Intermediate Similarity	NPC162193
0.8239	Intermediate Similarity	NPC478085
0.8231	Intermediate Similarity	NPC171932
0.8231	Intermediate Similarity	NPC28440
0.8231	Intermediate Similarity	NPC50250
0.8228	Intermediate Similarity	NPC175082
0.8227	Intermediate Similarity	NPC261619
0.8227	Intermediate Similarity	NPC61477
0.8227	Intermediate Similarity	NPC126029
0.8227	Intermediate Similarity	NPC185604
0.8227	Intermediate Similarity	NPC78770
0.8227	Intermediate Similarity	NPC219876
0.8227	Intermediate Similarity	NPC15658
0.8219	Intermediate Similarity	NPC469559
0.8219	Intermediate Similarity	NPC230538
0.8219	Intermediate Similarity	NPC229172
0.8219	Intermediate Similarity	NPC189115

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 NPC193920 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	358
0.1-0.2	846
0.2-0.3	1787
0.3-0.4	2737
0.4-0.5	1727
0.5-0.6	1012
0.6-0.7	600
0.7-0.8	79
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8269	Intermediate Similarity	NPD3787	Discontinued
0.8227	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8227	Intermediate Similarity	NPD1613	Approved
0.8201	Intermediate Similarity	NPD4908	Phase 1
0.8176	Intermediate Similarity	NPD3751	Discontinued
0.8088	Intermediate Similarity	NPD1091	Approved
0.8085	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8027	Intermediate Similarity	NPD6674	Discontinued
0.8	Intermediate Similarity	NPD2861	Phase 2
0.7956	Intermediate Similarity	NPD1610	Phase 2
0.7943	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7887	Intermediate Similarity	NPD4625	Phase 3
0.7872	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7762	Intermediate Similarity	NPD3027	Phase 3
0.7727	Intermediate Similarity	NPD1653	Approved
0.7714	Intermediate Similarity	NPD4749	Approved
0.7708	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7664	Intermediate Similarity	NPD1548	Phase 1
0.7647	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD37	Approved
0.764	Intermediate Similarity	NPD7199	Phase 2
0.7622	Intermediate Similarity	NPD7228	Approved
0.761	Intermediate Similarity	NPD4967	Phase 2
0.761	Intermediate Similarity	NPD4965	Approved
0.761	Intermediate Similarity	NPD4966	Approved
0.7603	Intermediate Similarity	NPD4060	Phase 1
0.7595	Intermediate Similarity	NPD8455	Phase 2
0.7576	Intermediate Similarity	NPD5844	Phase 1
0.7516	Intermediate Similarity	NPD6234	Discontinued
0.747	Intermediate Similarity	NPD7054	Approved
0.7453	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD5735	Approved
0.7431	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD7472	Approved
0.7425	Intermediate Similarity	NPD7074	Phase 3
0.7417	Intermediate Similarity	NPD5763	Approved
0.7417	Intermediate Similarity	NPD5762	Approved
0.7391	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD3892	Phase 2
0.7381	Intermediate Similarity	NPD6797	Phase 2
0.7338	Intermediate Similarity	NPD2677	Approved
0.7337	Intermediate Similarity	NPD7251	Discontinued
0.7337	Intermediate Similarity	NPD7240	Approved
0.7333	Intermediate Similarity	NPD7097	Phase 1
0.7324	Intermediate Similarity	NPD3705	Approved
0.7319	Intermediate Similarity	NPD6671	Approved
0.7315	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD5124	Phase 1
0.7303	Intermediate Similarity	NPD7266	Discontinued
0.7294	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD7808	Phase 3
0.729	Intermediate Similarity	NPD5058	Phase 3
0.7289	Intermediate Similarity	NPD6166	Phase 2
0.7289	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD4108	Discontinued
0.7273	Intermediate Similarity	NPD3750	Approved
0.7267	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD8312	Approved
0.7251	Intermediate Similarity	NPD8313	Approved
0.7248	Intermediate Similarity	NPD2238	Phase 2
0.7248	Intermediate Similarity	NPD4140	Approved
0.7244	Intermediate Similarity	NPD7212	Phase 2
0.7244	Intermediate Similarity	NPD7213	Phase 3
0.7239	Intermediate Similarity	NPD290	Approved
0.723	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD5402	Approved
0.7219	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD4536	Approved
0.7219	Intermediate Similarity	NPD4538	Approved
0.7212	Intermediate Similarity	NPD6959	Discontinued
0.7208	Intermediate Similarity	NPD1652	Phase 2
0.7205	Intermediate Similarity	NPD1934	Approved
0.7202	Intermediate Similarity	NPD3818	Discontinued
0.7197	Intermediate Similarity	NPD7447	Phase 1
0.7194	Intermediate Similarity	NPD709	Approved
0.7183	Intermediate Similarity	NPD5125	Phase 3
0.7183	Intermediate Similarity	NPD5126	Approved
0.7181	Intermediate Similarity	NPD6233	Phase 2
0.7172	Intermediate Similarity	NPD8651	Approved
0.7171	Intermediate Similarity	NPD5588	Approved
0.7171	Intermediate Similarity	NPD5960	Phase 3
0.7164	Intermediate Similarity	NPD968	Approved
0.716	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD2231	Phase 2
0.7153	Intermediate Similarity	NPD2235	Phase 2
0.7135	Intermediate Similarity	NPD6559	Discontinued
0.7133	Intermediate Similarity	NPD3620	Phase 2
0.7133	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD3496	Discontinued
0.7124	Intermediate Similarity	NPD6099	Approved
0.7124	Intermediate Similarity	NPD6100	Approved
0.7114	Intermediate Similarity	NPD6798	Discontinued
0.7103	Intermediate Similarity	NPD5327	Phase 3
0.7093	Intermediate Similarity	NPD7549	Discontinued
0.7089	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD7446	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD6355	Discontinued
0.7083	Intermediate Similarity	NPD1611	Approved
0.7081	Intermediate Similarity	NPD4380	Phase 2
0.7078	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7076	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD7157	Approved
0.7066	Intermediate Similarity	NPD7229	Phase 3
0.7063	Intermediate Similarity	NPD5846	Approved
0.7063	Intermediate Similarity	NPD6516	Phase 2
0.7062	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD3748	Approved
0.7059	Intermediate Similarity	NPD2155	Approved
0.7059	Intermediate Similarity	NPD2156	Approved
0.7059	Intermediate Similarity	NPD2154	Approved
0.7059	Intermediate Similarity	NPD2684	Approved
0.7055	Intermediate Similarity	NPD1465	Phase 2
0.7055	Intermediate Similarity	NPD7819	Suspended
0.7055	Intermediate Similarity	NPD2801	Approved
0.7051	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD4869	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD5283	Phase 1
0.7047	Intermediate Similarity	NPD7095	Approved
0.7044	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD6653	Approved
0.7027	Intermediate Similarity	NPD3018	Phase 2
0.7025	Intermediate Similarity	NPD7041	Phase 2
0.7025	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD1511	Approved
0.7012	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD2797	Approved
0.7007	Intermediate Similarity	NPD3094	Phase 2
0.7	Intermediate Similarity	NPD5403	Approved
0.6993	Remote Similarity	NPD1357	Approved
0.6987	Remote Similarity	NPD5177	Phase 3
0.6978	Remote Similarity	NPD7843	Approved
0.6971	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD422	Phase 1
0.6959	Remote Similarity	NPD6584	Phase 3
0.6949	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD7033	Discontinued
0.6946	Remote Similarity	NPD5494	Approved
0.6943	Remote Similarity	NPD7466	Approved
0.6939	Remote Similarity	NPD6696	Suspended
0.6939	Remote Similarity	NPD3225	Approved
0.6937	Remote Similarity	NPD1512	Approved
0.6933	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD4663	Approved
0.6928	Remote Similarity	NPD4097	Suspended
0.6928	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD6353	Approved
0.6923	Remote Similarity	NPD1549	Phase 2
0.6923	Remote Similarity	NPD7037	Approved
0.6923	Remote Similarity	NPD2970	Approved
0.6923	Remote Similarity	NPD2969	Approved
0.6909	Remote Similarity	NPD3817	Phase 2
0.6908	Remote Similarity	NPD5837	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD7340	Approved
0.6887	Remote Similarity	NPD6812	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD3268	Approved
0.6884	Remote Similarity	NPD4750	Phase 3
0.6883	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD7119	Phase 2
0.6882	Remote Similarity	NPD27	Approved
0.6882	Remote Similarity	NPD2489	Approved
0.6879	Remote Similarity	NPD7007	Discovery
0.6875	Remote Similarity	NPD5401	Approved
0.6875	Remote Similarity	NPD5585	Approved
0.6871	Remote Similarity	NPD2982	Phase 2
0.6871	Remote Similarity	NPD3685	Discontinued
0.6871	Remote Similarity	NPD2983	Phase 2
0.6867	Remote Similarity	NPD7768	Phase 2
0.6864	Remote Similarity	NPD3051	Approved
0.6864	Remote Similarity	NPD6232	Discontinued
0.6857	Remote Similarity	NPD5535	Approved
0.6849	Remote Similarity	NPD3092	Approved
0.6848	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD7473	Discontinued
0.6839	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD4628	Phase 3
0.6832	Remote Similarity	NPD6273	Approved
0.6832	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD7411	Suspended
0.6828	Remote Similarity	NPD4626	Approved
0.6826	Remote Similarity	NPD3749	Approved
0.6826	Remote Similarity	NPD7075	Discontinued
0.6818	Remote Similarity	NPD8053	Approved
0.6818	Remote Similarity	NPD8054	Approved
0.6815	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD2424	Discontinued
0.6813	Remote Similarity	NPD6087	Phase 1
0.6813	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD1398	Phase 1
0.6805	Remote Similarity	NPD8127	Discontinued
0.6803	Remote Similarity	NPD2233	Approved
0.6803	Remote Similarity	NPD2981	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