NPASS Compound

Structure

NPC28669 OpenBabel07101719122D 26 28 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 -0.9749 4.2714 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 -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 -3.1656 2.5245 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 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 -2.7317 3.4254 0.0000 C 0 0 2 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 -2.7317 0.6235 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.1656 1.5245 0.0000 C 0 0 2 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 0.4339 4.9499 0.0000 O 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 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 -3.7289 0.6982 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 3 2 0 0 0 0 2 9 1 0 0 0 0 3 10 1 0 0 0 0 4 8 1 0 0 0 0 5 9 1 0 0 0 0 5 11 1 0 0 0 0 6 10 1 0 0 0 0 7 12 2 0 0 0 0 7 13 1 0 0 0 0 8 1 1 1 0 0 0 8 25 1 0 0 0 0 9 20 2 0 0 0 0 10 21 1 6 0 0 0 11 16 2 0 0 0 0 11 17 1 0 0 0 0 12 16 1 0 0 0 0 12 22 1 0 0 0 0 13 17 2 0 0 0 0 13 23 1 0 0 0 0 14 4 1 1 0 0 0 14 15 1 0 0 0 0 14 26 1 0 0 0 0 15 6 1 6 0 0 0 15 26 1 0 0 0 0 16 18 1 0 0 0 0 17 19 1 0 0 0 0 18 24 2 0 0 0 0 18 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	382.08
Volume:	355.139
LogP:	2.519
LogD:	0.982
LogS:	-2.465
# Rotatable Bonds:	0
TPSA:	113.43
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.522
Synthetic Accessibility Score:	4.481
Fsp3:	0.5
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:	-5.274
MDCK Permeability:	1.935536420205608e-05
Pgp-inhibitor:	0.121
Pgp-substrate:	0.91
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.02
30% Bioavailability (F30%):	0.009

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.05
Plasma Protein Binding (PPB):	84.75414276123047%
Volume Distribution (VD):	0.822
Pgp-substrate:	6.448652744293213%

ADMET: Metabolism

CYP1A2-inhibitor:	0.164
CYP1A2-substrate:	0.095
CYP2C19-inhibitor:	0.057
CYP2C19-substrate:	0.064
CYP2C9-inhibitor:	0.471
CYP2C9-substrate:	0.955
CYP2D6-inhibitor:	0.222
CYP2D6-substrate:	0.222
CYP3A4-inhibitor:	0.367
CYP3A4-substrate:	0.214

ADMET: Excretion

Clearance (CL):	14.46
Half-life (T1/2):	0.918

ADMET: Toxicity

hERG Blockers:	0.05
Human Hepatotoxicity (H-HT):	0.207
Drug-inuced Liver Injury (DILI):	0.936
AMES Toxicity:	0.588
Rat Oral Acute Toxicity:	0.699
Maximum Recommended Daily Dose:	0.832
Skin Sensitization:	0.662
Carcinogencity:	0.078
Eye Corrosion:	0.004
Eye Irritation:	0.081
Respiratory Toxicity:	0.812

Download Data

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

Natural Product: NPC28669

Natural Product ID:	NPC28669
*Common Name:**	Pochonin B
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	BDHDUOMSMIFYEX-BHSJHAFESA-N
Standard InCHI:	InChI=1S/C18H19ClO7/c1-8-4-14-15(26-14)6-10(21)3-2-9(20)5-11-16(18(24)25-8)12(22)7-13(23)17(11)19/h2-3,7-8,10,14-15,21-23H,4-6H2,1H3/b3-2+/t8-,10+,14+,15+/m0/s1
SMILES:	C[C@H]1C[C@@H]2[C@@H](C[C@@H](/C=C/C(=O)Cc3c(c(cc(c3Cl)O)O)C(=O)O1)O)O2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL468030
PubChem CID:	6478911
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000176] Benzoic acids and derivatives [CHEMONTID:0001248] Hydroxybenzoic acid derivatives

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO12185	Humicola fuscoatra	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12444718]
NPO27821.1	Pochonia chlamydosporia	Under-species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[12828470]
NPO12185	Humicola fuscoatra	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24495105]
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
EC50	1
IC50	1
Others	1

Activity Type	# Activity
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT190	Organism	Human herpesvirus 1	Human herpesvirus 1	IC50	=	10000.0	nM	PMID[572071]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	Activity	=	98.0	%	PMID[572072]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	39600.0	nM	PMID[572072]

☑ 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 NPC28669 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	396
0.1-0.2	1856
0.2-0.3	5118
0.3-0.4	11241
0.4-0.5	7685
0.5-0.6	6578
0.6-0.7	8096
0.7-0.8	1647
0.8-0.85	57
0.85-0.9	7
0.9-0.95	7
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
0.9936	High Similarity	NPC173352
0.9936	High Similarity	NPC58653
0.9808	High Similarity	NPC473696
0.9744	High Similarity	NPC298401
0.9682	High Similarity	NPC474096
0.9623	High Similarity	NPC474061
0.962	High Similarity	NPC470081
0.9441	High Similarity	NPC472032
0.9427	High Similarity	NPC472404
0.925	High Similarity	NPC472405
0.8846	High Similarity	NPC257558
0.8782	High Similarity	NPC210966
0.8782	High Similarity	NPC478203
0.8782	High Similarity	NPC126882
0.859	High Similarity	NPC478201
0.859	High Similarity	NPC472035
0.8538	High Similarity	NPC470422
0.85	High Similarity	NPC472036
0.848	Intermediate Similarity	NPC474857
0.8471	Intermediate Similarity	NPC313123
0.8471	Intermediate Similarity	NPC478217
0.8466	Intermediate Similarity	NPC470103
0.8397	Intermediate Similarity	NPC478200
0.8397	Intermediate Similarity	NPC9121
0.8397	Intermediate Similarity	NPC177307
0.8397	Intermediate Similarity	NPC33144
0.8385	Intermediate Similarity	NPC477569
0.8382	Intermediate Similarity	NPC264922
0.8375	Intermediate Similarity	NPC83272
0.8375	Intermediate Similarity	NPC472034
0.8365	Intermediate Similarity	NPC478202
0.8344	Intermediate Similarity	NPC56204
0.8324	Intermediate Similarity	NPC470100
0.8323	Intermediate Similarity	NPC472033
0.8305	Intermediate Similarity	NPC99937
0.8291	Intermediate Similarity	NPC158472
0.8284	Intermediate Similarity	NPC245122
0.8282	Intermediate Similarity	NPC477567
0.8282	Intermediate Similarity	NPC477566
0.828	Intermediate Similarity	NPC212693
0.828	Intermediate Similarity	NPC94248
0.828	Intermediate Similarity	NPC472403
0.828	Intermediate Similarity	NPC475974
0.828	Intermediate Similarity	NPC191835
0.8268	Intermediate Similarity	NPC136411
0.825	Intermediate Similarity	NPC354984
0.8239	Intermediate Similarity	NPC158634
0.8239	Intermediate Similarity	NPC471801
0.8239	Intermediate Similarity	NPC244923
0.8235	Intermediate Similarity	NPC470563
0.8232	Intermediate Similarity	NPC221185
0.8222	Intermediate Similarity	NPC470099
0.8217	Intermediate Similarity	NPC474771
0.8217	Intermediate Similarity	NPC149372
0.8217	Intermediate Similarity	NPC65837
0.8217	Intermediate Similarity	NPC474849
0.8217	Intermediate Similarity	NPC178467
0.8217	Intermediate Similarity	NPC70380
0.821	Intermediate Similarity	NPC107625
0.8208	Intermediate Similarity	NPC277865
0.8187	Intermediate Similarity	NPC247104
0.8187	Intermediate Similarity	NPC474385
0.8176	Intermediate Similarity	NPC470561
0.8167	Intermediate Similarity	NPC316091
0.8144	Intermediate Similarity	NPC99381
0.8142	Intermediate Similarity	NPC48822
0.8141	Intermediate Similarity	NPC474097
0.8137	Intermediate Similarity	NPC51106
0.8121	Intermediate Similarity	NPC469670
0.8121	Intermediate Similarity	NPC469619
0.8113	Intermediate Similarity	NPC474655
0.8113	Intermediate Similarity	NPC32360
0.8113	Intermediate Similarity	NPC268052
0.8113	Intermediate Similarity	NPC139634
0.8113	Intermediate Similarity	NPC92655
0.8113	Intermediate Similarity	NPC52358
0.8113	Intermediate Similarity	NPC105456
0.811	Intermediate Similarity	NPC240622
0.811	Intermediate Similarity	NPC471641
0.811	Intermediate Similarity	NPC240253
0.811	Intermediate Similarity	NPC471642
0.811	Intermediate Similarity	NPC73411
0.811	Intermediate Similarity	NPC215711
0.8101	Intermediate Similarity	NPC71256
0.8095	Intermediate Similarity	NPC280497
0.8087	Intermediate Similarity	NPC214901
0.8086	Intermediate Similarity	NPC280404
0.8086	Intermediate Similarity	NPC86373
0.8086	Intermediate Similarity	NPC277426
0.8086	Intermediate Similarity	NPC210425
0.8077	Intermediate Similarity	NPC153783
0.8077	Intermediate Similarity	NPC43627
0.8068	Intermediate Similarity	NPC477568
0.8066	Intermediate Similarity	NPC313386
0.8065	Intermediate Similarity	NPC108744
0.8057	Intermediate Similarity	NPC470560
0.8056	Intermediate Similarity	NPC191606
0.805	Intermediate Similarity	NPC472602
0.8049	Intermediate Similarity	NPC210320
0.8038	Intermediate Similarity	NPC235115
0.8033	Intermediate Similarity	NPC220369
0.8025	Intermediate Similarity	NPC472006
0.8023	Intermediate Similarity	NPC45072
0.8012	Intermediate Similarity	NPC475730
0.8012	Intermediate Similarity	NPC472604
0.8012	Intermediate Similarity	NPC1704
0.8012	Intermediate Similarity	NPC67650
0.8012	Intermediate Similarity	NPC472603
0.8012	Intermediate Similarity	NPC472605
0.8012	Intermediate Similarity	NPC53649
0.8	Intermediate Similarity	NPC470565
0.8	Intermediate Similarity	NPC153417
0.8	Intermediate Similarity	NPC470559
0.8	Intermediate Similarity	NPC313541
0.8	Intermediate Similarity	NPC470562
0.7977	Intermediate Similarity	NPC68850
0.7975	Intermediate Similarity	NPC151607
0.7975	Intermediate Similarity	NPC42540
0.7967	Intermediate Similarity	NPC471812
0.7967	Intermediate Similarity	NPC471804
0.7967	Intermediate Similarity	NPC471803
0.795	Intermediate Similarity	NPC472601
0.795	Intermediate Similarity	NPC472600
0.7949	Intermediate Similarity	NPC219892
0.7949	Intermediate Similarity	NPC189823
0.7941	Intermediate Similarity	NPC197326
0.7933	Intermediate Similarity	NPC306240
0.7927	Intermediate Similarity	NPC312789
0.7923	Intermediate Similarity	NPC39409
0.7914	Intermediate Similarity	NPC154720
0.7914	Intermediate Similarity	NPC471731
0.7914	Intermediate Similarity	NPC469542
0.7914	Intermediate Similarity	NPC159721
0.7889	Intermediate Similarity	NPC151292
0.7882	Intermediate Similarity	NPC472623
0.7882	Intermediate Similarity	NPC470564
0.788	Intermediate Similarity	NPC471810
0.788	Intermediate Similarity	NPC471806
0.788	Intermediate Similarity	NPC471807
0.7879	Intermediate Similarity	NPC473023
0.7877	Intermediate Similarity	NPC471802
0.7875	Intermediate Similarity	NPC194579
0.7875	Intermediate Similarity	NPC135837
0.7862	Intermediate Similarity	NPC27407
0.7862	Intermediate Similarity	NPC142027
0.7857	Intermediate Similarity	NPC70016
0.7857	Intermediate Similarity	NPC240768
0.7857	Intermediate Similarity	NPC215921
0.7857	Intermediate Similarity	NPC200773
0.7857	Intermediate Similarity	NPC91809
0.7853	Intermediate Similarity	NPC471733
0.7853	Intermediate Similarity	NPC188618
0.7853	Intermediate Similarity	NPC469579
0.7844	Intermediate Similarity	NPC476684
0.7844	Intermediate Similarity	NPC84142
0.784	Intermediate Similarity	NPC155205
0.7836	Intermediate Similarity	NPC472889
0.7831	Intermediate Similarity	NPC14098
0.7826	Intermediate Similarity	NPC471805
0.7826	Intermediate Similarity	NPC121100
0.7826	Intermediate Similarity	NPC471813
0.7826	Intermediate Similarity	NPC221104
0.7824	Intermediate Similarity	NPC69043
0.7824	Intermediate Similarity	NPC472890
0.7824	Intermediate Similarity	NPC208173
0.7824	Intermediate Similarity	NPC478230
0.7824	Intermediate Similarity	NPC170189
0.7811	Intermediate Similarity	NPC76041
0.7811	Intermediate Similarity	NPC184284
0.7811	Intermediate Similarity	NPC115249
0.7811	Intermediate Similarity	NPC478224
0.7807	Intermediate Similarity	NPC198163
0.7805	Intermediate Similarity	NPC472610
0.7799	Intermediate Similarity	NPC175943
0.7798	Intermediate Similarity	NPC164762
0.7798	Intermediate Similarity	NPC472891
0.7797	Intermediate Similarity	NPC107283
0.7791	Intermediate Similarity	NPC37530
0.7791	Intermediate Similarity	NPC90411
0.7791	Intermediate Similarity	NPC470842
0.7784	Intermediate Similarity	NPC221352
0.7778	Intermediate Similarity	NPC247409
0.7778	Intermediate Similarity	NPC88269
0.7778	Intermediate Similarity	NPC275356
0.7765	Intermediate Similarity	NPC137301
0.7756	Intermediate Similarity	NPC41263
0.775	Intermediate Similarity	NPC180905
0.775	Intermediate Similarity	NPC182496
0.7744	Intermediate Similarity	NPC471644
0.7744	Intermediate Similarity	NPC250755
0.7744	Intermediate Similarity	NPC471640
0.7738	Intermediate Similarity	NPC270160
0.7738	Intermediate Similarity	NPC237440
0.7733	Intermediate Similarity	NPC478225
0.773	Intermediate Similarity	NPC99441
0.7725	Intermediate Similarity	NPC166583
0.7725	Intermediate Similarity	NPC53362
0.7725	Intermediate Similarity	NPC471734
0.7725	Intermediate Similarity	NPC81835
0.7722	Intermediate Similarity	NPC108278

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 NPC28669 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	350
0.1-0.2	1070
0.2-0.3	2098
0.3-0.4	2815
0.4-0.5	1839
0.5-0.6	721
0.6-0.7	243
0.7-0.8	14
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
0.7669	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD2403	Approved
0.75	Intermediate Similarity	NPD2532	Approved
0.75	Intermediate Similarity	NPD2534	Approved
0.75	Intermediate Similarity	NPD2533	Approved
0.7457	Intermediate Similarity	NPD7819	Suspended
0.7301	Intermediate Similarity	NPD230	Phase 1
0.7241	Intermediate Similarity	NPD7411	Suspended
0.7184	Intermediate Similarity	NPD4380	Phase 2
0.7169	Intermediate Similarity	NPD1510	Phase 2
0.716	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1549	Phase 2
0.7135	Intermediate Similarity	NPD7075	Discontinued
0.7135	Intermediate Similarity	NPD6799	Approved
0.7134	Intermediate Similarity	NPD1240	Approved
0.7119	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7102	Intermediate Similarity	NPD1934	Approved
0.7093	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7088	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD4363	Phase 3
0.7083	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD4360	Phase 2
0.7083	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD6232	Discontinued
0.7069	Intermediate Similarity	NPD2370	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD3750	Approved
0.7051	Intermediate Similarity	NPD9545	Approved
0.7049	Intermediate Similarity	NPD7473	Discontinued
0.7048	Intermediate Similarity	NPD1607	Approved
0.7039	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD2935	Discontinued
0.7024	Intermediate Similarity	NPD2796	Approved
0.7022	Intermediate Similarity	NPD3817	Phase 2
0.7017	Intermediate Similarity	NPD6959	Discontinued
0.7006	Intermediate Similarity	NPD6801	Discontinued
0.6989	Remote Similarity	NPD6599	Discontinued
0.6983	Remote Similarity	NPD3882	Suspended
0.6973	Remote Similarity	NPD5844	Phase 1
0.6966	Remote Similarity	NPD2801	Approved
0.6964	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD958	Approved
0.6944	Remote Similarity	NPD3749	Approved
0.6936	Remote Similarity	NPD1511	Approved
0.6932	Remote Similarity	NPD3226	Approved
0.6927	Remote Similarity	NPD5402	Approved
0.6923	Remote Similarity	NPD1551	Phase 2
0.6923	Remote Similarity	NPD9493	Approved
0.6919	Remote Similarity	NPD3818	Discontinued
0.6902	Remote Similarity	NPD6166	Phase 2
0.6902	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6902	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD1578	Phase 2
0.6889	Remote Similarity	NPD7768	Phase 2
0.6889	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD5710	Approved
0.6885	Remote Similarity	NPD5711	Approved
0.6882	Remote Similarity	NPD7054	Approved
0.6875	Remote Similarity	NPD957	Approved
0.6872	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD4361	Phase 2
0.6857	Remote Similarity	NPD1512	Approved
0.6845	Remote Similarity	NPD7472	Approved
0.6845	Remote Similarity	NPD7074	Phase 3
0.6839	Remote Similarity	NPD7390	Discontinued
0.6833	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD454	Approved
0.6826	Remote Similarity	NPD943	Approved
0.6825	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD5403	Approved
0.6809	Remote Similarity	NPD6797	Phase 2
0.6807	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.68	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD7251	Discontinued
0.6772	Remote Similarity	NPD6559	Discontinued
0.6765	Remote Similarity	NPD3748	Approved
0.6763	Remote Similarity	NPD4628	Phase 3
0.6737	Remote Similarity	NPD7808	Phase 3
0.6725	Remote Similarity	NPD5404	Approved
0.6725	Remote Similarity	NPD5405	Approved
0.6725	Remote Similarity	NPD5406	Approved
0.6725	Remote Similarity	NPD5408	Approved
0.6723	Remote Similarity	NPD920	Approved
0.6718	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD3764	Approved
0.6705	Remote Similarity	NPD5401	Approved
0.6705	Remote Similarity	NPD2800	Approved
0.6702	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD5494	Approved
0.6684	Remote Similarity	NPD8150	Discontinued
0.6649	Remote Similarity	NPD3751	Discontinued
0.6648	Remote Similarity	NPD2379	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD5953	Discontinued
0.6632	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD3887	Approved
0.6629	Remote Similarity	NPD6190	Approved
0.6626	Remote Similarity	NPD9269	Phase 2
0.6626	Remote Similarity	NPD9717	Approved
0.6614	Remote Similarity	NPD7286	Phase 2
0.661	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD1243	Approved
0.6593	Remote Similarity	NPD1465	Phase 2
0.6591	Remote Similarity	NPD643	Clinical (unspecified phase)
0.659	Remote Similarity	NPD2346	Discontinued
0.6588	Remote Similarity	NPD447	Suspended
0.6584	Remote Similarity	NPD9268	Approved
0.6573	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.657	Remote Similarity	NPD2799	Discontinued
0.655	Remote Similarity	NPD6651	Approved
0.6541	Remote Similarity	NPD919	Approved
0.6534	Remote Similarity	NPD2354	Approved
0.6524	Remote Similarity	NPD3787	Discontinued
0.6519	Remote Similarity	NPD4972	Discontinued
0.6509	Remote Similarity	NPD411	Approved
0.6506	Remote Similarity	NPD1470	Approved
0.6506	Remote Similarity	NPD1203	Approved
0.65	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD1184	Approved
0.6488	Remote Similarity	NPD6832	Phase 2
0.6471	Remote Similarity	NPD1247	Approved
0.6464	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6463	Remote Similarity	NPD1201	Approved
0.6462	Remote Similarity	NPD6784	Approved
0.6462	Remote Similarity	NPD6785	Approved
0.6448	Remote Similarity	NPD37	Approved
0.6447	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6443	Remote Similarity	NPD8312	Approved
0.6443	Remote Similarity	NPD8313	Approved
0.6437	Remote Similarity	NPD6099	Approved
0.6437	Remote Similarity	NPD6100	Approved
0.6432	Remote Similarity	NPD4966	Approved
0.6432	Remote Similarity	NPD4967	Phase 2
0.6432	Remote Similarity	NPD4965	Approved
0.6425	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.642	Remote Similarity	NPD2654	Approved
0.6412	Remote Similarity	NPD3268	Approved
0.641	Remote Similarity	NPD74	Approved
0.641	Remote Similarity	NPD9266	Approved
0.6407	Remote Similarity	NPD1164	Approved
0.6404	Remote Similarity	NPD4914	Approved
0.64	Remote Similarity	NPD6312	Discontinued
0.64	Remote Similarity	NPD6534	Approved
0.64	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.64	Remote Similarity	NPD6535	Approved
0.64	Remote Similarity	NPD2353	Approved
0.64	Remote Similarity	NPD2344	Approved
0.6394	Remote Similarity	NPD8151	Discontinued
0.6392	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.639	Remote Similarity	NPD7435	Discontinued
0.6383	Remote Similarity	NPD7199	Phase 2
0.6379	Remote Similarity	NPD7033	Discontinued
0.6369	Remote Similarity	NPD1019	Discontinued
0.6364	Remote Similarity	NPD6234	Discontinued
0.6364	Remote Similarity	NPD422	Phase 1
0.6359	Remote Similarity	NPD8320	Phase 1
0.6359	Remote Similarity	NPD8319	Approved
0.6353	Remote Similarity	NPD2598	Clinical (unspecified phase)
0.6349	Remote Similarity	NPD7229	Phase 3
0.6346	Remote Similarity	NPD9267	Approved
0.6346	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD9264	Approved
0.6346	Remote Similarity	NPD9263	Approved
0.6345	Remote Similarity	NPD8434	Phase 2
0.634	Remote Similarity	NPD7685	Pre-registration
0.6337	Remote Similarity	NPD4915	Approved
0.6324	Remote Similarity	NPD6777	Approved
0.6324	Remote Similarity	NPD6779	Approved
0.6324	Remote Similarity	NPD6776	Approved
0.6324	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6324	Remote Similarity	NPD6781	Approved
0.6324	Remote Similarity	NPD6780	Approved
0.6324	Remote Similarity	NPD6782	Approved
0.6324	Remote Similarity	NPD6778	Approved
0.6316	Remote Similarity	NPD2313	Discontinued
0.6316	Remote Similarity	NPD3926	Phase 2
0.6305	Remote Similarity	NPD7699	Phase 2
0.6305	Remote Similarity	NPD7700	Phase 2
0.6298	Remote Similarity	NPD6273	Approved
0.6298	Remote Similarity	NPD6973	Clinical (unspecified phase)
0.629	Remote Similarity	NPD4288	Approved
0.629	Remote Similarity	NPD5353	Approved
0.6272	Remote Similarity	NPD2798	Approved
0.6271	Remote Similarity	NPD4534	Discontinued
0.6262	Remote Similarity	NPD4386	Approved
0.6262	Remote Similarity	NPD4387	Approved
0.6257	Remote Similarity	NPD2309	Approved
0.6256	Remote Similarity	NPD4388	Approved
0.6256	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6242	Remote Similarity	NPD4626	Approved
0.6232	Remote Similarity	NPD7697	Approved
0.6232	Remote Similarity	NPD7696	Phase 3
0.6232	Remote Similarity	NPD7698	Approved
0.623	Remote Similarity	NPD7184	Clinical (unspecified phase)

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