NPASS Compound

Structure

NPC470081 OpenBabel07101718272D 26 27 0 0 1 0 0 0 0 0999 V2000 -0.9749 -1.2225 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1656 2.5245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9499 4.0489 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1656 1.5245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9749 4.2714 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9499 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7818 3.4254 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9478 1.5245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9749 -0.2225 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.7317 3.4254 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.7317 0.6235 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 4.0489 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2157 2.5245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0817 1.0245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9478 2.5245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2157 1.5245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0817 3.0245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7818 0.6235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0817 4.0245 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 -3.5135 4.0489 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5135 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4339 4.9499 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0817 0.0245 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8138 3.0245 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5637 -0.0000 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 2 4 2 0 0 0 0 2 10 1 0 0 0 0 3 5 1 0 0 0 0 3 10 1 0 0 0 0 4 11 1 0 0 0 0 5 12 1 0 0 0 0 6 9 1 0 0 0 0 6 11 1 0 0 0 0 7 12 1 0 0 0 0 7 13 1 0 0 0 0 8 14 2 0 0 0 0 8 15 1 0 0 0 0 9 1 1 6 0 0 0 9 26 1 0 0 0 0 10 20 1 6 0 0 0 11 21 1 1 0 0 0 12 22 2 0 0 0 0 13 16 2 0 0 0 0 13 17 1 0 0 0 0 14 16 1 0 0 0 0 14 23 1 0 0 0 0 15 17 2 0 0 0 0 15 24 1 0 0 0 0 16 18 1 0 0 0 0 17 19 1 0 0 0 0 18 25 2 0 0 0 0 18 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	384.1
Volume:	363.695
LogP:	1.988
LogD:	0.082
LogS:	-2.442
# Rotatable Bonds:	0
TPSA:	124.29
# H-Bond Aceptor:	7
# H-Bond Donor:	4
# Rings:	2
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.397
Synthetic Accessibility Score:	4.521
Fsp3:	0.444
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:	-5.92
MDCK Permeability:	5.589827196672559e-06
Pgp-inhibitor:	0.003
Pgp-substrate:	0.996
Human Intestinal Absorption (HIA):	0.019
20% Bioavailability (F20%):	0.977
30% Bioavailability (F30%):	0.978

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.074
Plasma Protein Binding (PPB):	86.53036499023438%
Volume Distribution (VD):	0.555
Pgp-substrate:	10.042180061340332%

ADMET: Metabolism

CYP1A2-inhibitor:	0.423
CYP1A2-substrate:	0.128
CYP2C19-inhibitor:	0.091
CYP2C19-substrate:	0.079
CYP2C9-inhibitor:	0.531
CYP2C9-substrate:	0.964
CYP2D6-inhibitor:	0.206
CYP2D6-substrate:	0.2
CYP3A4-inhibitor:	0.221
CYP3A4-substrate:	0.172

ADMET: Excretion

Clearance (CL):	9.163
Half-life (T1/2):	0.906

ADMET: Toxicity

hERG Blockers:	0.054
Human Hepatotoxicity (H-HT):	0.821
Drug-inuced Liver Injury (DILI):	0.966
AMES Toxicity:	0.093
Rat Oral Acute Toxicity:	0.23
Maximum Recommended Daily Dose:	0.977
Skin Sensitization:	0.375
Carcinogencity:	0.101
Eye Corrosion:	0.003
Eye Irritation:	0.051
Respiratory Toxicity:	0.682

Download Data

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

Natural Product: NPC470081

Natural Product ID:	NPC470081
*Common Name:**	Pochonin N
IUPAC Name:	(6R,7Z,9R,11R)-18-chloro-6,9,15,17-tetrahydroxy-11-methyl-12-oxabicyclo[12.4.0]octadeca-1(14),7,15,17-tetraene-3,13-dione
Synonyms:	Pochonin N
Standard InCHIKey:	UGYZEXDMXHEULY-SLTYSDCVSA-N
Standard InCHI:	InChI=1S/C18H21ClO7/c1-9-6-11(21)4-2-10(20)3-5-12(22)7-13-16(18(25)26-9)14(23)8-15(24)17(13)19/h2,4,8-11,20-21,23-24H,3,5-7H2,1H3/b4-2-/t9-,10+,11+/m1/s1
SMILES:	C[C@@H]1C[C@H](/C=C[C@@H](CCC(=O)Cc2c(c(cc(c2Cl)O)O)C(=O)O1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1684401
PubChem CID:	53320828
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000147] Macrolides and analogues

*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
NPO21538	Fusarium sp.	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11076576]
NPO12185	Humicola fuscoatra	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12444718]
NPO21538	Fusarium sp.	Species	Nectriaceae	Eukaryota	Melia azedarach	n.a.	n.a.	PMID[21353539]
NPO21538	Fusarium sp.	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24183988]
NPO12185	Humicola fuscoatra	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24495105]
NPO21538	Fusarium sp.	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[33180497]
NPO21538	Fusarium sp.	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8988601]
NPO21538	Fusarium sp.	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12185	Humicola fuscoatra	Species	Chaetomiaceae	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
Others	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT140	Organism	Artemia	Artemia	Activity	=	82.8	%	PMID[523032]

☑ 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 NPC470081 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	376
0.1-0.2	1804
0.2-0.3	4682
0.3-0.4	10974
0.4-0.5	8142
0.5-0.6	5978
0.6-0.7	7920
0.7-0.8	2660
0.8-0.85	135
0.85-0.9	9
0.9-0.95	11
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9806	High Similarity	NPC473696
0.9742	High Similarity	NPC298401
0.962	High Similarity	NPC474061
0.962	High Similarity	NPC28669
0.956	High Similarity	NPC472032
0.9557	High Similarity	NPC173352
0.9557	High Similarity	NPC58653
0.9554	High Similarity	NPC474096
0.9423	High Similarity	NPC472404
0.9245	High Similarity	NPC472405
0.8701	High Similarity	NPC313123
0.8701	High Similarity	NPC478217
0.869	High Similarity	NPC474857
0.8639	High Similarity	NPC470422
0.8608	High Similarity	NPC477569
0.859	High Similarity	NPC478202
0.8581	High Similarity	NPC472035
0.8581	High Similarity	NPC478201
0.8563	High Similarity	NPC470103
0.8506	High Similarity	NPC191835
0.8506	High Similarity	NPC33144
0.8506	High Similarity	NPC212693
0.8506	High Similarity	NPC475974
0.8506	High Similarity	NPC478200
0.8506	High Similarity	NPC94248
0.8506	High Similarity	NPC99937
0.85	High Similarity	NPC477567
0.85	High Similarity	NPC477566
0.8494	Intermediate Similarity	NPC245122
0.8481	Intermediate Similarity	NPC257558
0.848	Intermediate Similarity	NPC264922
0.8443	Intermediate Similarity	NPC470563
0.8442	Intermediate Similarity	NPC178467
0.8442	Intermediate Similarity	NPC70380
0.8442	Intermediate Similarity	NPC474771
0.8442	Intermediate Similarity	NPC149372
0.8442	Intermediate Similarity	NPC65837
0.8442	Intermediate Similarity	NPC474849
0.8428	Intermediate Similarity	NPC472033
0.8418	Intermediate Similarity	NPC478203
0.8418	Intermediate Similarity	NPC126882
0.8418	Intermediate Similarity	NPC210966
0.8418	Intermediate Similarity	NPC470100
0.8412	Intermediate Similarity	NPC277865
0.8397	Intermediate Similarity	NPC158472
0.8387	Intermediate Similarity	NPC9121
0.8387	Intermediate Similarity	NPC177307
0.8383	Intermediate Similarity	NPC470561
0.8375	Intermediate Similarity	NPC472036
0.8365	Intermediate Similarity	NPC83272
0.8365	Intermediate Similarity	NPC472034
0.8354	Intermediate Similarity	NPC472006
0.8344	Intermediate Similarity	NPC158634
0.8333	Intermediate Similarity	NPC474655
0.8333	Intermediate Similarity	NPC105456
0.8333	Intermediate Similarity	NPC139634
0.8324	Intermediate Similarity	NPC45072
0.8324	Intermediate Similarity	NPC221185
0.8323	Intermediate Similarity	NPC71256
0.8315	Intermediate Similarity	NPC470099
0.8303	Intermediate Similarity	NPC280497
0.8291	Intermediate Similarity	NPC474385
0.8278	Intermediate Similarity	NPC247104
0.8269	Intermediate Similarity	NPC472602
0.8269	Intermediate Similarity	NPC472403
0.8258	Intermediate Similarity	NPC316091
0.8256	Intermediate Similarity	NPC470560
0.8239	Intermediate Similarity	NPC51106
0.8232	Intermediate Similarity	NPC48822
0.8229	Intermediate Similarity	NPC471801
0.8228	Intermediate Similarity	NPC472604
0.8228	Intermediate Similarity	NPC53649
0.8228	Intermediate Similarity	NPC1704
0.8228	Intermediate Similarity	NPC472605
0.8228	Intermediate Similarity	NPC472603
0.8228	Intermediate Similarity	NPC67650
0.8228	Intermediate Similarity	NPC244923
0.8221	Intermediate Similarity	NPC56204
0.8217	Intermediate Similarity	NPC32360
0.8217	Intermediate Similarity	NPC268052
0.821	Intermediate Similarity	NPC240253
0.821	Intermediate Similarity	NPC471642
0.821	Intermediate Similarity	NPC240622
0.821	Intermediate Similarity	NPC471641
0.8204	Intermediate Similarity	NPC470559
0.8199	Intermediate Similarity	NPC107625
0.8198	Intermediate Similarity	NPC470562
0.8198	Intermediate Similarity	NPC470565
0.8187	Intermediate Similarity	NPC42540
0.8187	Intermediate Similarity	NPC86373
0.8187	Intermediate Similarity	NPC277426
0.8187	Intermediate Similarity	NPC210425
0.8187	Intermediate Similarity	NPC151607
0.8187	Intermediate Similarity	NPC280404
0.8182	Intermediate Similarity	NPC153783
0.8177	Intermediate Similarity	NPC214901
0.8176	Intermediate Similarity	NPC68850
0.8165	Intermediate Similarity	NPC472600
0.8165	Intermediate Similarity	NPC472601
0.8161	Intermediate Similarity	NPC477568
0.8156	Intermediate Similarity	NPC313386
0.8156	Intermediate Similarity	NPC136411
0.8152	Intermediate Similarity	NPC108744
0.8148	Intermediate Similarity	NPC210320
0.8146	Intermediate Similarity	NPC191606
0.8141	Intermediate Similarity	NPC235115
0.8129	Intermediate Similarity	NPC474097
0.8125	Intermediate Similarity	NPC471731
0.8125	Intermediate Similarity	NPC469542
0.8125	Intermediate Similarity	NPC159721
0.8125	Intermediate Similarity	NPC354984
0.8122	Intermediate Similarity	NPC220369
0.8113	Intermediate Similarity	NPC475730
0.811	Intermediate Similarity	NPC469670
0.811	Intermediate Similarity	NPC469619
0.8101	Intermediate Similarity	NPC92655
0.8101	Intermediate Similarity	NPC52358
0.8098	Intermediate Similarity	NPC215711
0.8098	Intermediate Similarity	NPC154720
0.8098	Intermediate Similarity	NPC153417
0.8098	Intermediate Similarity	NPC73411
0.8089	Intermediate Similarity	NPC194579
0.8087	Intermediate Similarity	NPC313541
0.8086	Intermediate Similarity	NPC473023
0.8084	Intermediate Similarity	NPC470564
0.8079	Intermediate Similarity	NPC151292
0.8077	Intermediate Similarity	NPC142027
0.8077	Intermediate Similarity	NPC27407
0.8065	Intermediate Similarity	NPC43627
0.8063	Intermediate Similarity	NPC471733
0.8063	Intermediate Similarity	NPC469579
0.8061	Intermediate Similarity	NPC70016
0.8061	Intermediate Similarity	NPC200773
0.8061	Intermediate Similarity	NPC215921
0.8061	Intermediate Similarity	NPC240768
0.8052	Intermediate Similarity	NPC219892
0.8052	Intermediate Similarity	NPC189823
0.805	Intermediate Similarity	NPC155205
0.8037	Intermediate Similarity	NPC14098
0.8036	Intermediate Similarity	NPC197326
0.8025	Intermediate Similarity	NPC312789
0.8024	Intermediate Similarity	NPC99381
0.8023	Intermediate Similarity	NPC306240
0.8012	Intermediate Similarity	NPC472610
0.8	Intermediate Similarity	NPC37530
0.7989	Intermediate Similarity	NPC198163
0.7989	Intermediate Similarity	NPC107283
0.7988	Intermediate Similarity	NPC221352
0.7987	Intermediate Similarity	NPC275356
0.7987	Intermediate Similarity	NPC88269
0.7975	Intermediate Similarity	NPC135837
0.7956	Intermediate Similarity	NPC471804
0.7956	Intermediate Similarity	NPC471803
0.7956	Intermediate Similarity	NPC471812
0.795	Intermediate Similarity	NPC250755
0.7939	Intermediate Similarity	NPC476684
0.7939	Intermediate Similarity	NPC4423
0.7939	Intermediate Similarity	NPC77325
0.7937	Intermediate Similarity	NPC99441
0.7927	Intermediate Similarity	NPC166583
0.7927	Intermediate Similarity	NPC53362
0.7927	Intermediate Similarity	NPC471734
0.7925	Intermediate Similarity	NPC221104
0.7914	Intermediate Similarity	NPC473692
0.7912	Intermediate Similarity	NPC39409
0.7911	Intermediate Similarity	NPC291454
0.7911	Intermediate Similarity	NPC158481
0.7904	Intermediate Similarity	NPC478224
0.7901	Intermediate Similarity	NPC474499
0.7901	Intermediate Similarity	NPC471639
0.7901	Intermediate Similarity	NPC471643
0.7901	Intermediate Similarity	NPC200207
0.7898	Intermediate Similarity	NPC175943
0.7892	Intermediate Similarity	NPC472891
0.7892	Intermediate Similarity	NPC60413
0.7888	Intermediate Similarity	NPC90411
0.7888	Intermediate Similarity	NPC470842
0.7885	Intermediate Similarity	NPC476389
0.7875	Intermediate Similarity	NPC247409
0.7871	Intermediate Similarity	NPC247477
0.7871	Intermediate Similarity	NPC17840
0.7869	Intermediate Similarity	NPC471806
0.7869	Intermediate Similarity	NPC471810
0.7869	Intermediate Similarity	NPC471807
0.7866	Intermediate Similarity	NPC471735
0.7865	Intermediate Similarity	NPC471802
0.7862	Intermediate Similarity	NPC301915
0.7862	Intermediate Similarity	NPC261292
0.7857	Intermediate Similarity	NPC41263
0.7848	Intermediate Similarity	NPC182496
0.7848	Intermediate Similarity	NPC180905
0.7844	Intermediate Similarity	NPC91809
0.7841	Intermediate Similarity	NPC188618
0.784	Intermediate Similarity	NPC96692
0.784	Intermediate Similarity	NPC471644
0.784	Intermediate Similarity	NPC82913
0.784	Intermediate Similarity	NPC49108
0.784	Intermediate Similarity	NPC471640
0.7831	Intermediate Similarity	NPC237440
0.7831	Intermediate Similarity	NPC84142

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 NPC470081 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	329
0.1-0.2	1051
0.2-0.3	1970
0.3-0.4	2808
0.4-0.5	1863
0.5-0.6	830
0.6-0.7	268
0.7-0.8	31
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
0.7764	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7759	Intermediate Similarity	NPD2403	Approved
0.7697	Intermediate Similarity	NPD2533	Approved
0.7697	Intermediate Similarity	NPD2532	Approved
0.7697	Intermediate Similarity	NPD2534	Approved
0.7544	Intermediate Similarity	NPD7819	Suspended
0.7326	Intermediate Similarity	NPD7411	Suspended
0.7299	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD230	Phase 1
0.7273	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD1510	Phase 2
0.7247	Intermediate Similarity	NPD6232	Discontinued
0.7246	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD1549	Phase 2
0.7222	Intermediate Similarity	NPD7473	Discontinued
0.7222	Intermediate Similarity	NPD1240	Approved
0.7216	Intermediate Similarity	NPD7075	Discontinued
0.7184	Intermediate Similarity	NPD1934	Approved
0.7176	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD4380	Phase 2
0.7167	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD4360	Phase 2
0.7158	Intermediate Similarity	NPD4363	Phase 3
0.7152	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD2370	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3750	Approved
0.7143	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD1607	Approved
0.7119	Intermediate Similarity	NPD3749	Approved
0.7118	Intermediate Similarity	NPD6799	Approved
0.7108	Intermediate Similarity	NPD2796	Approved
0.7095	Intermediate Similarity	NPD6959	Discontinued
0.7086	Intermediate Similarity	NPD6801	Discontinued
0.7069	Intermediate Similarity	NPD6599	Discontinued
0.7062	Intermediate Similarity	NPD3882	Suspended
0.7056	Intermediate Similarity	NPD5710	Approved
0.7056	Intermediate Similarity	NPD5711	Approved
0.7048	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD2801	Approved
0.7032	Intermediate Similarity	NPD9545	Approved
0.7031	Intermediate Similarity	NPD4361	Phase 2
0.7031	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD943	Approved
0.7011	Intermediate Similarity	NPD3226	Approved
0.7006	Intermediate Similarity	NPD2935	Discontinued
0.7006	Intermediate Similarity	NPD3817	Phase 2
0.6995	Remote Similarity	NPD3818	Discontinued
0.6988	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD6166	Phase 2
0.6978	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD1578	Phase 2
0.6966	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD7768	Phase 2
0.6957	Remote Similarity	NPD5844	Phase 1
0.6932	Remote Similarity	NPD958	Approved
0.6919	Remote Similarity	NPD1511	Approved
0.6919	Remote Similarity	NPD7390	Discontinued
0.6919	Remote Similarity	NPD7074	Phase 3
0.6914	Remote Similarity	NPD454	Approved
0.691	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.691	Remote Similarity	NPD5402	Approved
0.6905	Remote Similarity	NPD1551	Phase 2
0.6903	Remote Similarity	NPD9493	Approved
0.6898	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.689	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.689	Remote Similarity	NPD3764	Approved
0.6882	Remote Similarity	NPD2800	Approved
0.6879	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6865	Remote Similarity	NPD7054	Approved
0.6857	Remote Similarity	NPD957	Approved
0.6845	Remote Similarity	NPD3748	Approved
0.6842	Remote Similarity	NPD4628	Phase 3
0.6839	Remote Similarity	NPD1512	Approved
0.6828	Remote Similarity	NPD7472	Approved
0.6805	Remote Similarity	NPD5405	Approved
0.6805	Remote Similarity	NPD5404	Approved
0.6805	Remote Similarity	NPD5406	Approved
0.6805	Remote Similarity	NPD5408	Approved
0.68	Remote Similarity	NPD920	Approved
0.68	Remote Similarity	NPD5403	Approved
0.6791	Remote Similarity	NPD5953	Discontinued
0.6791	Remote Similarity	NPD6797	Phase 2
0.6788	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6758	Remote Similarity	NPD5494	Approved
0.6755	Remote Similarity	NPD6559	Discontinued
0.6755	Remote Similarity	NPD7251	Discontinued
0.6754	Remote Similarity	NPD8150	Discontinued
0.6746	Remote Similarity	NPD2799	Discontinued
0.6726	Remote Similarity	NPD6651	Approved
0.6722	Remote Similarity	NPD2379	Clinical (unspecified phase)
0.672	Remote Similarity	NPD7808	Phase 3
0.6705	Remote Similarity	NPD3887	Approved
0.6702	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD1470	Approved
0.6686	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD5401	Approved
0.6686	Remote Similarity	NPD1243	Approved
0.6684	Remote Similarity	NPD7286	Phase 2
0.6667	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2346	Discontinued
0.6667	Remote Similarity	NPD1465	Phase 2
0.6647	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD1201	Approved
0.6612	Remote Similarity	NPD919	Approved
0.6611	Remote Similarity	NPD37	Approved
0.6609	Remote Similarity	NPD6190	Approved
0.6609	Remote Similarity	NPD2354	Approved
0.6608	Remote Similarity	NPD6099	Approved
0.6608	Remote Similarity	NPD6100	Approved
0.6605	Remote Similarity	NPD9269	Phase 2
0.6605	Remote Similarity	NPD9717	Approved
0.6593	Remote Similarity	NPD4965	Approved
0.6593	Remote Similarity	NPD4967	Phase 2
0.6593	Remote Similarity	NPD4966	Approved
0.6592	Remote Similarity	NPD4972	Discontinued
0.6591	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD3268	Approved
0.6582	Remote Similarity	NPD405	Clinical (unspecified phase)
0.657	Remote Similarity	NPD2344	Approved
0.6568	Remote Similarity	NPD1184	Approved
0.6568	Remote Similarity	NPD447	Suspended
0.6566	Remote Similarity	NPD4915	Approved
0.6562	Remote Similarity	NPD9268	Approved
0.6554	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.655	Remote Similarity	NPD4914	Approved
0.655	Remote Similarity	NPD7033	Discontinued
0.6545	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD7199	Phase 2
0.6541	Remote Similarity	NPD1247	Approved
0.6536	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD6234	Discontinued
0.6517	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6513	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.651	Remote Similarity	NPD8313	Approved
0.651	Remote Similarity	NPD8312	Approved
0.6505	Remote Similarity	NPD7229	Phase 3
0.6494	Remote Similarity	NPD2654	Approved
0.6488	Remote Similarity	NPD411	Approved
0.6485	Remote Similarity	NPD1164	Approved
0.6485	Remote Similarity	NPD1203	Approved
0.6474	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD2353	Approved
0.6471	Remote Similarity	NPD3926	Phase 2
0.6468	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD6832	Phase 2
0.6465	Remote Similarity	NPD6534	Approved
0.6465	Remote Similarity	NPD6312	Discontinued
0.6465	Remote Similarity	NPD6535	Approved
0.6456	Remote Similarity	NPD8151	Discontinued
0.6455	Remote Similarity	NPD3751	Discontinued
0.6453	Remote Similarity	NPD7435	Discontinued
0.6443	Remote Similarity	NPD6785	Approved
0.6443	Remote Similarity	NPD6784	Approved
0.6442	Remote Similarity	NPD422	Phase 1
0.6437	Remote Similarity	NPD4534	Discontinued
0.6422	Remote Similarity	NPD8320	Phase 1
0.6422	Remote Similarity	NPD8319	Approved
0.642	Remote Similarity	NPD2309	Approved
0.642	Remote Similarity	NPD4626	Approved
0.6417	Remote Similarity	NPD3787	Discontinued
0.641	Remote Similarity	NPD8434	Phase 2
0.6404	Remote Similarity	NPD4386	Approved
0.6404	Remote Similarity	NPD4387	Approved
0.6402	Remote Similarity	NPD1608	Approved
0.64	Remote Similarity	NPD4388	Approved
0.6391	Remote Similarity	NPD2313	Discontinued
0.6387	Remote Similarity	NPD74	Approved
0.6387	Remote Similarity	NPD9266	Approved
0.6386	Remote Similarity	NPD6778	Approved
0.6386	Remote Similarity	NPD6776	Approved
0.6386	Remote Similarity	NPD6779	Approved
0.6386	Remote Similarity	NPD6777	Approved
0.6386	Remote Similarity	NPD6780	Approved
0.6386	Remote Similarity	NPD6782	Approved
0.6386	Remote Similarity	NPD6781	Approved
0.6383	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD5124	Phase 1
0.6374	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6369	Remote Similarity	NPD6273	Approved
0.6368	Remote Similarity	NPD7228	Approved
0.6368	Remote Similarity	NPD7700	Phase 2
0.6368	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6368	Remote Similarity	NPD7699	Phase 2
0.6359	Remote Similarity	NPD4288	Approved
0.6359	Remote Similarity	NPD6973	Clinical (unspecified phase)
0.6358	Remote Similarity	NPD5691	Approved
0.6349	Remote Similarity	NPD5822	Clinical (unspecified phase)
0.6348	Remote Similarity	NPD7040	Clinical (unspecified phase)
0.6348	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6348	Remote Similarity	NPD7041	Phase 2
0.6347	Remote Similarity	NPD2798	Approved
0.6345	Remote Similarity	NPD4287	Approved
0.6343	Remote Similarity	NPD5958	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