NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	254.12
Volume:	258.253
LogP:	1.456
LogD:	1.247
LogS:	-1.928
# Rotatable Bonds:	5
TPSA:	86.99
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	1
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.693
Synthetic Accessibility Score:	2.759
Fsp3:	0.462
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.51
MDCK Permeability:	1.9534658349584788e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.018
Human Intestinal Absorption (HIA):	0.116
20% Bioavailability (F20%):	0.009
30% Bioavailability (F30%):	0.543

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.923
Plasma Protein Binding (PPB):	64.7443618774414%
Volume Distribution (VD):	0.592
Pgp-substrate:	23.378131866455078%

ADMET: Metabolism

CYP1A2-inhibitor:	0.195
CYP1A2-substrate:	0.362
CYP2C19-inhibitor:	0.037
CYP2C19-substrate:	0.317
CYP2C9-inhibitor:	0.037
CYP2C9-substrate:	0.752
CYP2D6-inhibitor:	0.023
CYP2D6-substrate:	0.363
CYP3A4-inhibitor:	0.015
CYP3A4-substrate:	0.192

ADMET: Excretion

Clearance (CL):	11.23
Half-life (T1/2):	0.906

ADMET: Toxicity

hERG Blockers:	0.018
Human Hepatotoxicity (H-HT):	0.052
Drug-inuced Liver Injury (DILI):	0.434
AMES Toxicity:	0.029
Rat Oral Acute Toxicity:	0.025
Maximum Recommended Daily Dose:	0.037
Skin Sensitization:	0.062
Carcinogencity:	0.025
Eye Corrosion:	0.004
Eye Irritation:	0.345
Respiratory Toxicity:	0.024

Download Data

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

Natural Product: NPC473777

Natural Product ID:	NPC473777
*Common Name:**	Hostmaniane
IUPAC Name:	methyl 3-(2,3-dihydroxy-3-methylbutyl)-4-hydroxybenzoate
Synonyms:	hostmaniane
Standard InCHIKey:	ABFHVQPVDSMGNR-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C13H18O5/c1-13(2,17)11(15)7-9-6-8(12(16)18-3)4-5-10(9)14/h4-6,11,14-15,17H,7H2,1-3H3
SMILES:	CC(C)(C(CC1=C(C=CC(=C1)C(=O)OC)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL451571
PubChem CID:	11184361
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000176] Benzoic acids and derivatives [CHEMONTID:0001350] Benzoic acid esters [CHEMONTID:0004701] p-Hydroxybenzoic acid esters [CHEMONTID:0004702] p-Hydroxybenzoic acid alkyl esters

*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
NPO33179	piper sp.	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15568762]

☑ 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	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT487	Organism	Cladosporium cladosporioides	Cladosporium cladosporioides	Activity	=	0.5	ug	PMID[511505]
NPT488	Organism	Cladosporium sphaerospermum	Cladosporium sphaerospermum	Activity	=	0.5	ug	PMID[511505]

☑ 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 NPC473777 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	1225
0.2-0.3	3084
0.3-0.4	7043
0.4-0.5	11163
0.5-0.6	4537
0.6-0.7	8405
0.7-0.8	6546
0.8-0.85	369
0.85-0.9	26
0.9-0.95	9
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9758	High Similarity	NPC473744
0.9453	High Similarity	NPC302844
0.9313	High Similarity	NPC475111
0.928	High Similarity	NPC184219
0.9274	High Similarity	NPC67300
0.9179	High Similarity	NPC469911
0.912	High Similarity	NPC475192
0.9111	High Similarity	NPC184053
0.9084	High Similarity	NPC239855
0.8984	High Similarity	NPC110211
0.8915	High Similarity	NPC121104
0.8872	High Similarity	NPC204582
0.8837	High Similarity	NPC204579
0.88	High Similarity	NPC473767
0.8759	High Similarity	NPC64664
0.872	High Similarity	NPC27633
0.872	High Similarity	NPC273282
0.872	High Similarity	NPC94298
0.872	High Similarity	NPC474890
0.872	High Similarity	NPC161943
0.871	High Similarity	NPC131192
0.8657	High Similarity	NPC114116
0.8636	High Similarity	NPC226855
0.8626	High Similarity	NPC158654
0.8615	High Similarity	NPC49938
0.8613	High Similarity	NPC112135
0.8611	High Similarity	NPC11892
0.8582	High Similarity	NPC97188
0.8571	High Similarity	NPC109778
0.856	High Similarity	NPC83718
0.855	High Similarity	NPC476022
0.855	High Similarity	NPC473751
0.855	High Similarity	NPC474945
0.8521	High Similarity	NPC316769
0.8521	High Similarity	NPC473023
0.8511	High Similarity	NPC213900
0.8489	Intermediate Similarity	NPC158472
0.8483	Intermediate Similarity	NPC475093
0.8478	Intermediate Similarity	NPC221104
0.8467	Intermediate Similarity	NPC291454
0.8467	Intermediate Similarity	NPC84699
0.8462	Intermediate Similarity	NPC222298
0.8462	Intermediate Similarity	NPC51070
0.8451	Intermediate Similarity	NPC83272
0.8433	Intermediate Similarity	NPC163169
0.8433	Intermediate Similarity	NPC327457
0.8433	Intermediate Similarity	NPC86774
0.8433	Intermediate Similarity	NPC123
0.8429	Intermediate Similarity	NPC470842
0.8425	Intermediate Similarity	NPC256141
0.8421	Intermediate Similarity	NPC2596
0.8421	Intermediate Similarity	NPC2401
0.8414	Intermediate Similarity	NPC37642
0.8409	Intermediate Similarity	NPC95309
0.8403	Intermediate Similarity	NPC17600
0.8394	Intermediate Similarity	NPC142027
0.8394	Intermediate Similarity	NPC164136
0.8392	Intermediate Similarity	NPC469498
0.838	Intermediate Similarity	NPC469683
0.838	Intermediate Similarity	NPC113397
0.8369	Intermediate Similarity	NPC321980
0.8369	Intermediate Similarity	NPC470087
0.8359	Intermediate Similarity	NPC61779
0.8358	Intermediate Similarity	NPC194979
0.8357	Intermediate Similarity	NPC327187
0.8345	Intermediate Similarity	NPC212693
0.8345	Intermediate Similarity	NPC126739
0.8345	Intermediate Similarity	NPC94248
0.8345	Intermediate Similarity	NPC197666
0.8345	Intermediate Similarity	NPC52931
0.8333	Intermediate Similarity	NPC53362
0.8333	Intermediate Similarity	NPC326847
0.8333	Intermediate Similarity	NPC66991
0.8333	Intermediate Similarity	NPC156892
0.8333	Intermediate Similarity	NPC14875
0.8333	Intermediate Similarity	NPC81835
0.8333	Intermediate Similarity	NPC166583
0.8322	Intermediate Similarity	NPC474044
0.8322	Intermediate Similarity	NPC258856
0.8322	Intermediate Similarity	NPC75295
0.8321	Intermediate Similarity	NPC174991
0.832	Intermediate Similarity	NPC242136
0.831	Intermediate Similarity	NPC469615
0.8298	Intermediate Similarity	NPC472605
0.8298	Intermediate Similarity	NPC472604
0.8288	Intermediate Similarity	NPC179178
0.8288	Intermediate Similarity	NPC56204
0.8288	Intermediate Similarity	NPC180351
0.8286	Intermediate Similarity	NPC105456
0.8286	Intermediate Similarity	NPC473988
0.8286	Intermediate Similarity	NPC139634
0.8276	Intermediate Similarity	NPC161955
0.8273	Intermediate Similarity	NPC194579
0.8273	Intermediate Similarity	NPC170718
0.8273	Intermediate Similarity	NPC70380
0.8271	Intermediate Similarity	NPC474944
0.8271	Intermediate Similarity	NPC475236
0.8264	Intermediate Similarity	NPC286038
0.8261	Intermediate Similarity	NPC70680
0.8261	Intermediate Similarity	NPC18646
0.8261	Intermediate Similarity	NPC475029
0.8261	Intermediate Similarity	NPC233350
0.8261	Intermediate Similarity	NPC182217
0.8261	Intermediate Similarity	NPC476018
0.8261	Intermediate Similarity	NPC27407
0.8258	Intermediate Similarity	NPC221798
0.8255	Intermediate Similarity	NPC471787
0.8252	Intermediate Similarity	NPC151607
0.8252	Intermediate Similarity	NPC476178
0.8252	Intermediate Similarity	NPC280404
0.8252	Intermediate Similarity	NPC301751
0.8252	Intermediate Similarity	NPC86373
0.8252	Intermediate Similarity	NPC117836
0.8252	Intermediate Similarity	NPC51887
0.8252	Intermediate Similarity	NPC277426
0.8252	Intermediate Similarity	NPC210425
0.8252	Intermediate Similarity	NPC475705
0.8252	Intermediate Similarity	NPC245482
0.8252	Intermediate Similarity	NPC42540
0.8248	Intermediate Similarity	NPC283823
0.8248	Intermediate Similarity	NPC213485
0.8248	Intermediate Similarity	NPC304929
0.8248	Intermediate Similarity	NPC40524
0.8248	Intermediate Similarity	NPC159418
0.8248	Intermediate Similarity	NPC477280
0.8248	Intermediate Similarity	NPC1321
0.8248	Intermediate Similarity	NPC156124
0.8248	Intermediate Similarity	NPC19719
0.8248	Intermediate Similarity	NPC139074
0.8248	Intermediate Similarity	NPC477281
0.8244	Intermediate Similarity	NPC291189
0.8244	Intermediate Similarity	NPC69403
0.8239	Intermediate Similarity	NPC478250
0.8239	Intermediate Similarity	NPC82913
0.8239	Intermediate Similarity	NPC470089
0.8235	Intermediate Similarity	NPC264145
0.8235	Intermediate Similarity	NPC104854
0.8231	Intermediate Similarity	NPC472422
0.8231	Intermediate Similarity	NPC263384
0.8231	Intermediate Similarity	NPC244577
0.8231	Intermediate Similarity	NPC472420
0.8231	Intermediate Similarity	NPC471676
0.8231	Intermediate Similarity	NPC474744
0.8231	Intermediate Similarity	NPC472423
0.8231	Intermediate Similarity	NPC474772
0.8227	Intermediate Similarity	NPC470211
0.8227	Intermediate Similarity	NPC472601
0.8227	Intermediate Similarity	NPC472600
0.8222	Intermediate Similarity	NPC94810
0.8222	Intermediate Similarity	NPC170546
0.8222	Intermediate Similarity	NPC939
0.8222	Intermediate Similarity	NPC66246
0.8219	Intermediate Similarity	NPC104172
0.8219	Intermediate Similarity	NPC247219
0.8219	Intermediate Similarity	NPC270160
0.8219	Intermediate Similarity	NPC89442
0.8219	Intermediate Similarity	NPC237440
0.8219	Intermediate Similarity	NPC88886
0.8214	Intermediate Similarity	NPC478200
0.8214	Intermediate Similarity	NPC191835
0.8214	Intermediate Similarity	NPC33144
0.8209	Intermediate Similarity	NPC37512
0.8207	Intermediate Similarity	NPC91902
0.8207	Intermediate Similarity	NPC202494
0.8207	Intermediate Similarity	NPC473133
0.8207	Intermediate Similarity	NPC85773
0.8207	Intermediate Similarity	NPC47388
0.8207	Intermediate Similarity	NPC470670
0.8201	Intermediate Similarity	NPC471345
0.8201	Intermediate Similarity	NPC158481
0.8195	Intermediate Similarity	NPC165556
0.8195	Intermediate Similarity	NPC472592
0.8194	Intermediate Similarity	NPC257558
0.8188	Intermediate Similarity	NPC27643
0.8188	Intermediate Similarity	NPC68517
0.8182	Intermediate Similarity	NPC471731
0.8182	Intermediate Similarity	NPC51106
0.8182	Intermediate Similarity	NPC473090
0.8182	Intermediate Similarity	NPC271451
0.8182	Intermediate Similarity	NPC159721
0.8182	Intermediate Similarity	NPC148545
0.8175	Intermediate Similarity	NPC111888
0.8169	Intermediate Similarity	NPC158634
0.8169	Intermediate Similarity	NPC130485
0.8169	Intermediate Similarity	NPC244923
0.8169	Intermediate Similarity	NPC478201
0.8169	Intermediate Similarity	NPC478217
0.8169	Intermediate Similarity	NPC313123
0.8169	Intermediate Similarity	NPC472603
0.8169	Intermediate Similarity	NPC472035
0.8163	Intermediate Similarity	NPC472421
0.8163	Intermediate Similarity	NPC469619
0.8163	Intermediate Similarity	NPC289021
0.8163	Intermediate Similarity	NPC469670
0.8163	Intermediate Similarity	NPC158546
0.8162	Intermediate Similarity	NPC307732
0.8162	Intermediate Similarity	NPC282230
0.8162	Intermediate Similarity	NPC42292
0.8162	Intermediate Similarity	NPC245395
0.8162	Intermediate Similarity	NPC183348

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 NPC473777 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	250
0.1-0.2	821
0.2-0.3	1625
0.3-0.4	2551
0.4-0.5	2046
0.5-0.6	1177
0.6-0.7	539
0.7-0.8	135
0.8-0.85	5
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.872	High Similarity	NPD9545	Approved
0.8298	Intermediate Similarity	NPD4628	Phase 3
0.8248	Intermediate Similarity	NPD230	Phase 1
0.8227	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8041	Intermediate Similarity	NPD4380	Phase 2
0.8014	Intermediate Similarity	NPD2935	Discontinued
0.7984	Intermediate Similarity	NPD9493	Approved
0.7984	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7961	Intermediate Similarity	NPD7075	Discontinued
0.7899	Intermediate Similarity	NPD3764	Approved
0.7881	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7817	Intermediate Similarity	NPD1510	Phase 2
0.7815	Intermediate Similarity	NPD6801	Discontinued
0.7786	Intermediate Similarity	NPD1240	Approved
0.7763	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD6190	Approved
0.7703	Intermediate Similarity	NPD2533	Approved
0.7703	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7703	Intermediate Similarity	NPD2534	Approved
0.7703	Intermediate Similarity	NPD2532	Approved
0.7676	Intermediate Similarity	NPD1607	Approved
0.7669	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7662	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7655	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7655	Intermediate Similarity	NPD1549	Phase 2
0.7635	Intermediate Similarity	NPD6799	Approved
0.7632	Intermediate Similarity	NPD7411	Suspended
0.7616	Intermediate Similarity	NPD7458	Discontinued
0.7613	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD9269	Phase 2
0.7569	Intermediate Similarity	NPD2799	Discontinued
0.7554	Intermediate Similarity	NPD9494	Approved
0.7551	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7536	Intermediate Similarity	NPD1164	Approved
0.7532	Intermediate Similarity	NPD7819	Suspended
0.7518	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD5844	Phase 1
0.7468	Intermediate Similarity	NPD1934	Approved
0.7467	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7466	Intermediate Similarity	NPD6004	Phase 3
0.7466	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7466	Intermediate Similarity	NPD6002	Phase 3
0.7466	Intermediate Similarity	NPD6005	Phase 3
0.7466	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD6599	Discontinued
0.7448	Intermediate Similarity	NPD7033	Discontinued
0.7445	Intermediate Similarity	NPD9717	Approved
0.7436	Intermediate Similarity	NPD7768	Phase 2
0.7432	Intermediate Similarity	NPD3750	Approved
0.7432	Intermediate Similarity	NPD7003	Approved
0.7421	Intermediate Similarity	NPD6232	Discontinued
0.7413	Intermediate Similarity	NPD943	Approved
0.7407	Intermediate Similarity	NPD9268	Approved
0.7407	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD1551	Phase 2
0.7397	Intermediate Similarity	NPD2796	Approved
0.7394	Intermediate Similarity	NPD6798	Discontinued
0.7394	Intermediate Similarity	NPD2313	Discontinued
0.7372	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD920	Approved
0.7364	Intermediate Similarity	NPD9266	Approved
0.7364	Intermediate Similarity	NPD74	Approved
0.7361	Intermediate Similarity	NPD6355	Discontinued
0.7357	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD4626	Approved
0.7329	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7319	Intermediate Similarity	NPD1608	Approved
0.7287	Intermediate Similarity	NPD9264	Approved
0.7287	Intermediate Similarity	NPD9263	Approved
0.7287	Intermediate Similarity	NPD9267	Approved
0.7286	Intermediate Similarity	NPD1203	Approved
0.7285	Intermediate Similarity	NPD1511	Approved
0.7285	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD7473	Discontinued
0.7279	Intermediate Similarity	NPD5406	Approved
0.7279	Intermediate Similarity	NPD5404	Approved
0.7279	Intermediate Similarity	NPD5405	Approved
0.7279	Intermediate Similarity	NPD5408	Approved
0.7273	Intermediate Similarity	NPD3226	Approved
0.7273	Intermediate Similarity	NPD6559	Discontinued
0.7262	Intermediate Similarity	NPD8150	Discontinued
0.7261	Intermediate Similarity	NPD3817	Phase 2
0.7255	Intermediate Similarity	NPD5403	Approved
0.7248	Intermediate Similarity	NPD1243	Approved
0.7241	Intermediate Similarity	NPD447	Suspended
0.7241	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD5124	Phase 1
0.7239	Intermediate Similarity	NPD3818	Discontinued
0.7237	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD7266	Discontinued
0.723	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD1778	Approved
0.7222	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD6166	Phase 2
0.7222	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD3882	Suspended
0.7214	Intermediate Similarity	NPD1283	Approved
0.7212	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD4308	Phase 3
0.7211	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD8166	Discontinued
0.7197	Intermediate Similarity	NPD8455	Phase 2
0.7197	Intermediate Similarity	NPD2801	Approved
0.7194	Intermediate Similarity	NPD3972	Approved
0.7193	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD6651	Approved
0.719	Intermediate Similarity	NPD5049	Phase 3
0.719	Intermediate Similarity	NPD1512	Approved
0.7181	Intermediate Similarity	NPD2424	Discontinued
0.7172	Intermediate Similarity	NPD4060	Phase 1
0.7164	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD1470	Approved
0.7161	Intermediate Similarity	NPD3455	Phase 2
0.7161	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD1358	Approved
0.7153	Intermediate Similarity	NPD5691	Approved
0.7152	Intermediate Similarity	NPD2354	Approved
0.7152	Intermediate Similarity	NPD3887	Approved
0.7152	Intermediate Similarity	NPD7074	Phase 3
0.7152	Intermediate Similarity	NPD5402	Approved
0.7133	Intermediate Similarity	NPD2800	Approved
0.7133	Intermediate Similarity	NPD6832	Phase 2
0.7124	Intermediate Similarity	NPD5401	Approved
0.7124	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD1201	Approved
0.7122	Intermediate Similarity	NPD422	Phase 1
0.7121	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD2344	Approved
0.7114	Intermediate Similarity	NPD2346	Discontinued
0.7113	Intermediate Similarity	NPD2798	Approved
0.7113	Intermediate Similarity	NPD1019	Discontinued
0.7108	Intermediate Similarity	NPD5953	Discontinued
0.7103	Intermediate Similarity	NPD6233	Phase 2
0.7101	Intermediate Similarity	NPD17	Approved
0.7099	Intermediate Similarity	NPD2182	Approved
0.7099	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD3748	Approved
0.7091	Intermediate Similarity	NPD7054	Approved
0.7091	Intermediate Similarity	NPD7286	Phase 2
0.709	Intermediate Similarity	NPD1241	Discontinued
0.7089	Intermediate Similarity	NPD1465	Phase 2
0.7086	Intermediate Similarity	NPD3400	Discontinued
0.7083	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD6273	Approved
0.7076	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD1481	Phase 2
0.7066	Intermediate Similarity	NPD7685	Pre-registration
0.7063	Intermediate Similarity	NPD9495	Approved
0.7063	Intermediate Similarity	NPD3749	Approved
0.7054	Intermediate Similarity	NPD164	Approved
0.705	Intermediate Similarity	NPD3496	Discontinued
0.7048	Intermediate Similarity	NPD7472	Approved
0.7047	Intermediate Similarity	NPD4476	Approved
0.7047	Intermediate Similarity	NPD4477	Approved
0.7042	Intermediate Similarity	NPD2797	Approved
0.7037	Intermediate Similarity	NPD9281	Approved
0.7037	Intermediate Similarity	NPD2629	Approved
0.7037	Intermediate Similarity	NPD6959	Discontinued
0.7034	Intermediate Similarity	NPD3268	Approved
0.7034	Intermediate Similarity	NPD411	Approved
0.7032	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD1652	Phase 2
0.7019	Intermediate Similarity	NPD919	Approved
0.7013	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD6797	Phase 2
0.7006	Intermediate Similarity	NPD3823	Discontinued
0.7	Intermediate Similarity	NPD1535	Discovery
0.7	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1281	Approved
0.6994	Remote Similarity	NPD5710	Approved
0.6994	Remote Similarity	NPD5711	Approved
0.6993	Remote Similarity	NPD7236	Approved
0.6986	Remote Similarity	NPD4062	Phase 3
0.6982	Remote Similarity	NPD8312	Approved
0.6982	Remote Similarity	NPD8313	Approved
0.6977	Remote Similarity	NPD9261	Approved
0.6975	Remote Similarity	NPD5494	Approved
0.6968	Remote Similarity	NPD9509	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD3027	Phase 3
0.6966	Remote Similarity	NPD7008	Discontinued
0.6964	Remote Similarity	NPD7251	Discontinued
0.6962	Remote Similarity	NPD6386	Approved
0.6962	Remote Similarity	NPD6385	Approved
0.6962	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD8434	Phase 2
0.6948	Remote Similarity	NPD7390	Discontinued
0.6947	Remote Similarity	NPD3134	Approved
0.6939	Remote Similarity	NPD825	Approved
0.6939	Remote Similarity	NPD826	Approved
0.6939	Remote Similarity	NPD2979	Phase 3
0.6939	Remote Similarity	NPD4307	Phase 2
0.6934	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD3847	Discontinued

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