NPASS Compound

Structure

CID214901 OpenBabel06191716002D 28 30 0 0 0 0 0 0 0 0999 V2000 4.9860 1.4283 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1155 3.1555 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8650 -0.0747 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6228 -1.0990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5549 2.4040 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9916 1.5777 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5633 2.6282 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6228 2.9010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5521 2.3293 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4311 0.8262 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6228 -0.0990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9944 1.6525 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6228 1.9010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5605 2.5534 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.8019 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7568 0.4010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4888 0.4010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4888 1.4010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4339 0.9010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7568 1.4010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9749 -0.2225 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3548 -0.0990 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 -3.4888 3.4010 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1238 3.3797 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3548 1.9010 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1974 -1.1974 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9749 2.0245 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 9 1 0 0 0 0 2 9 1 0 0 0 0 3 10 1 0 0 0 0 4 11 1 0 0 0 0 5 6 1 0 0 0 0 5 9 2 0 0 0 0 6 12 1 0 0 0 0 7 14 2 0 0 0 0 7 15 1 0 0 0 0 8 13 1 0 0 0 0 8 23 2 0 0 0 0 10 12 2 0 0 0 0 10 19 1 0 0 0 0 11 16 2 0 0 0 0 11 17 1 0 0 0 0 12 14 1 0 0 0 0 13 18 1 0 0 0 0 13 20 2 0 0 0 0 14 24 1 0 0 0 0 15 19 2 0 0 0 0 15 27 1 0 0 0 0 16 20 1 0 0 0 0 16 21 1 0 0 0 0 17 18 2 0 0 0 0 17 22 1 0 0 0 0 18 25 1 0 0 0 0 19 28 1 0 0 0 0 20 27 1 0 0 0 0 21 26 2 0 0 0 0 21 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	402.09
Volume:	390.327
LogP:	6.36
LogD:	3.419
LogS:	-3.966
# Rotatable Bonds:	3
TPSA:	93.06
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.324
Synthetic Accessibility Score:	3.504
Fsp3:	0.238
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.927
MDCK Permeability:	1.9952127331634983e-05
Pgp-inhibitor:	0.022
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.214
20% Bioavailability (F20%):	0.829
30% Bioavailability (F30%):	0.001

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.015
Plasma Protein Binding (PPB):	100.3828125%
Volume Distribution (VD):	0.637
Pgp-substrate:	1.1082193851470947%

ADMET: Metabolism

CYP1A2-inhibitor:	0.586
CYP1A2-substrate:	0.15
CYP2C19-inhibitor:	0.636
CYP2C19-substrate:	0.107
CYP2C9-inhibitor:	0.833
CYP2C9-substrate:	0.846
CYP2D6-inhibitor:	0.015
CYP2D6-substrate:	0.209
CYP3A4-inhibitor:	0.154
CYP3A4-substrate:	0.123

ADMET: Excretion

Clearance (CL):	6.968
Half-life (T1/2):	0.22

ADMET: Toxicity

hERG Blockers:	0.001
Human Hepatotoxicity (H-HT):	0.054
Drug-inuced Liver Injury (DILI):	0.237
AMES Toxicity:	0.032
Rat Oral Acute Toxicity:	0.971
Maximum Recommended Daily Dose:	0.936
Skin Sensitization:	0.732
Carcinogencity:	0.509
Eye Corrosion:	0.007
Eye Irritation:	0.948
Respiratory Toxicity:	0.671

Download Data

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

Natural Product: NPC214901

Natural Product ID:	NPC214901
*Common Name:**	Mollicellin J
IUPAC Name:	8-chloro-2,9-dihydroxy-4,7-dimethyl-3-(3-methylbut-2-enyl)-6-oxobenzo[b][1,4]benzodioxepine-10-carbaldehyde
Synonyms:	Mollicellin J
Standard InCHIKey:	NKSQSZYYPUIJDD-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C21H19ClO6/c1-9(2)5-6-12-10(3)19-15(7-14(12)24)27-20-13(8-23)18(25)17(22)11(4)16(20)21(26)28-19/h5,7-8,24-25H,6H2,1-4H3
SMILES:	CC(=CCc1c(C)c2c(cc1O)Oc1c(C=O)c(c(c(C)c1C(=O)O2)Cl)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1080085
PubChem CID:	24787300
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0001645] Depsides and depsidones

*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
NPO30621	Chaetomium brasiliense	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19663417]
NPO30621	Chaetomium brasiliense	Species	Chaetomiaceae	Eukaryota	n.a.	Doi Inthanon, Jomtong District, Chiangmai Province, Thailand	2006-JUN	PMID[19663417]
NPO30621	Chaetomium brasiliense	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[CiteXplore Id]

☑ 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
IC50	3

Activity Type	# Activity
Cell Line	2
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	=	29.1	ug.mL-1	PMID[546628]
NPT639	Cell Line	NCI-H187	Homo sapiens	IC50	=	23.3	ug.mL-1	PMID[546628]
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	IC50	=	4.9	ug.mL-1	PMID[546628]

☑ 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 NPC214901 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	467
0.1-0.2	2249
0.2-0.3	5737
0.3-0.4	12617
0.4-0.5	4971
0.5-0.6	5224
0.6-0.7	6871
0.7-0.8	4396
0.8-0.85	111
0.85-0.9	45
0.9-0.95	5
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9943	High Similarity	NPC220369
0.9667	High Similarity	NPC154720
0.9556	High Similarity	NPC198163
0.9429	High Similarity	NPC471801
0.9235	High Similarity	NPC193676
0.9116	High Similarity	NPC471812
0.9116	High Similarity	NPC471803
0.9116	High Similarity	NPC471804
0.9045	High Similarity	NPC471802
0.9016	High Similarity	NPC471807
0.9016	High Similarity	NPC471810
0.9016	High Similarity	NPC471806
0.8971	High Similarity	NPC272485
0.8971	High Similarity	NPC292788
0.8962	High Similarity	NPC471813
0.8962	High Similarity	NPC471805
0.8962	High Similarity	NPC121100
0.8883	High Similarity	NPC108278
0.887	High Similarity	NPC246716
0.887	High Similarity	NPC239440
0.887	High Similarity	NPC20543
0.882	High Similarity	NPC188618
0.8814	High Similarity	NPC26568
0.88	High Similarity	NPC156082
0.8771	High Similarity	NPC181523
0.8764	High Similarity	NPC10576
0.8764	High Similarity	NPC1827
0.8757	High Similarity	NPC39409
0.875	High Similarity	NPC112981
0.8722	High Similarity	NPC139350
0.8722	High Similarity	NPC289147
0.8701	High Similarity	NPC20216
0.8696	High Similarity	NPC471811
0.8696	High Similarity	NPC471809
0.8674	High Similarity	NPC45072
0.8641	High Similarity	NPC195675
0.8641	High Similarity	NPC471808
0.8641	High Similarity	NPC471814
0.8626	High Similarity	NPC28160
0.8619	High Similarity	NPC477568
0.8579	High Similarity	NPC113446
0.8556	High Similarity	NPC17219
0.8508	High Similarity	NPC474857
0.8478	Intermediate Similarity	NPC329161
0.8478	Intermediate Similarity	NPC470091
0.8478	Intermediate Similarity	NPC240887
0.8462	Intermediate Similarity	NPC470422
0.8449	Intermediate Similarity	NPC474499
0.8418	Intermediate Similarity	NPC143050
0.8415	Intermediate Similarity	NPC264922
0.84	Intermediate Similarity	NPC471800
0.837	Intermediate Similarity	NPC175804
0.8368	Intermediate Similarity	NPC221185
0.8362	Intermediate Similarity	NPC83763
0.8362	Intermediate Similarity	NPC238381
0.8362	Intermediate Similarity	NPC168616
0.8352	Intermediate Similarity	NPC109827
0.8352	Intermediate Similarity	NPC277865
0.8352	Intermediate Similarity	NPC124470
0.8343	Intermediate Similarity	NPC472032
0.8333	Intermediate Similarity	NPC267153
0.8325	Intermediate Similarity	NPC247104
0.8324	Intermediate Similarity	NPC93739
0.8297	Intermediate Similarity	NPC49487
0.8297	Intermediate Similarity	NPC99613
0.8295	Intermediate Similarity	NPC89625
0.8295	Intermediate Similarity	NPC149618
0.8287	Intermediate Similarity	NPC29160
0.8278	Intermediate Similarity	NPC474350
0.8278	Intermediate Similarity	NPC284007
0.8278	Intermediate Similarity	NPC300984
0.8268	Intermediate Similarity	NPC303565
0.8263	Intermediate Similarity	NPC470099
0.8263	Intermediate Similarity	NPC470100
0.8245	Intermediate Similarity	NPC99937
0.8242	Intermediate Similarity	NPC234331
0.8232	Intermediate Similarity	NPC8070
0.8222	Intermediate Similarity	NPC474096
0.8207	Intermediate Similarity	NPC158226
0.8201	Intermediate Similarity	NPC191606
0.8197	Intermediate Similarity	NPC165979
0.8197	Intermediate Similarity	NPC163130
0.8182	Intermediate Similarity	NPC273483
0.8177	Intermediate Similarity	NPC234004
0.8177	Intermediate Similarity	NPC197168
0.8177	Intermediate Similarity	NPC470081
0.8167	Intermediate Similarity	NPC298401
0.8167	Intermediate Similarity	NPC66288
0.8146	Intermediate Similarity	NPC472456
0.8138	Intermediate Similarity	NPC151292
0.8132	Intermediate Similarity	NPC58653
0.8132	Intermediate Similarity	NPC25361
0.8132	Intermediate Similarity	NPC173352
0.8125	Intermediate Similarity	NPC133856
0.8122	Intermediate Similarity	NPC473696
0.8122	Intermediate Similarity	NPC8300
0.8115	Intermediate Similarity	NPC316091
0.8114	Intermediate Similarity	NPC233267
0.8114	Intermediate Similarity	NPC291049
0.8112	Intermediate Similarity	NPC108744
0.8111	Intermediate Similarity	NPC200594
0.8111	Intermediate Similarity	NPC475886
0.8111	Intermediate Similarity	NPC474287
0.8111	Intermediate Similarity	NPC47623
0.8101	Intermediate Similarity	NPC217677
0.8101	Intermediate Similarity	NPC165977
0.8093	Intermediate Similarity	NPC48822
0.8087	Intermediate Similarity	NPC472452
0.8087	Intermediate Similarity	NPC28669
0.8077	Intermediate Similarity	NPC236132
0.8077	Intermediate Similarity	NPC270837
0.8066	Intermediate Similarity	NPC474351
0.8066	Intermediate Similarity	NPC474186
0.8066	Intermediate Similarity	NPC474187
0.8066	Intermediate Similarity	NPC472405
0.8066	Intermediate Similarity	NPC475883
0.8057	Intermediate Similarity	NPC105415
0.8056	Intermediate Similarity	NPC45846
0.8054	Intermediate Similarity	NPC470562
0.8054	Intermediate Similarity	NPC470565
0.8051	Intermediate Similarity	NPC313541
0.8045	Intermediate Similarity	NPC54928
0.8033	Intermediate Similarity	NPC130920
0.8033	Intermediate Similarity	NPC68850
0.8033	Intermediate Similarity	NPC85057
0.8022	Intermediate Similarity	NPC294965
0.8022	Intermediate Similarity	NPC144843
0.8022	Intermediate Similarity	NPC108767
0.8021	Intermediate Similarity	NPC313386
0.8011	Intermediate Similarity	NPC228785
0.8011	Intermediate Similarity	NPC14353
0.8011	Intermediate Similarity	NPC470560
0.8011	Intermediate Similarity	NPC56085
0.801	Intermediate Similarity	NPC470103
0.8	Intermediate Similarity	NPC477569
0.8	Intermediate Similarity	NPC472404
0.7989	Intermediate Similarity	NPC474061
0.7989	Intermediate Similarity	NPC306240
0.7978	Intermediate Similarity	NPC7483
0.7978	Intermediate Similarity	NPC289968
0.7978	Intermediate Similarity	NPC199773
0.7967	Intermediate Similarity	NPC40491
0.7967	Intermediate Similarity	NPC278052
0.7967	Intermediate Similarity	NPC61010
0.7956	Intermediate Similarity	NPC85121
0.7956	Intermediate Similarity	NPC100123
0.7944	Intermediate Similarity	NPC280497
0.7944	Intermediate Similarity	NPC146211
0.7935	Intermediate Similarity	NPC326520
0.7933	Intermediate Similarity	NPC475895
0.7923	Intermediate Similarity	NPC229632
0.7923	Intermediate Similarity	NPC245122
0.7921	Intermediate Similarity	NPC204350
0.7912	Intermediate Similarity	NPC292415
0.7912	Intermediate Similarity	NPC36217
0.7912	Intermediate Similarity	NPC119224
0.7912	Intermediate Similarity	NPC299436
0.7912	Intermediate Similarity	NPC320359
0.791	Intermediate Similarity	NPC477566
0.791	Intermediate Similarity	NPC477567
0.7901	Intermediate Similarity	NPC300727
0.7901	Intermediate Similarity	NPC241904
0.7901	Intermediate Similarity	NPC223787
0.7901	Intermediate Similarity	NPC108456
0.7892	Intermediate Similarity	NPC37870
0.7892	Intermediate Similarity	NPC272502
0.7892	Intermediate Similarity	NPC170245
0.7892	Intermediate Similarity	NPC43319
0.7889	Intermediate Similarity	NPC20541
0.7886	Intermediate Similarity	NPC134621
0.788	Intermediate Similarity	NPC220313
0.788	Intermediate Similarity	NPC152659
0.788	Intermediate Similarity	NPC248638
0.788	Intermediate Similarity	NPC470563
0.788	Intermediate Similarity	NPC477689
0.788	Intermediate Similarity	NPC236521
0.7877	Intermediate Similarity	NPC175978
0.7877	Intermediate Similarity	NPC217447
0.7869	Intermediate Similarity	NPC103201
0.7869	Intermediate Similarity	NPC473106
0.7869	Intermediate Similarity	NPC349525
0.7865	Intermediate Similarity	NPC225129
0.7865	Intermediate Similarity	NPC213382
0.7865	Intermediate Similarity	NPC164527
0.7861	Intermediate Similarity	NPC107283
0.7857	Intermediate Similarity	NPC476242
0.7849	Intermediate Similarity	NPC6588
0.7849	Intermediate Similarity	NPC474024
0.7849	Intermediate Similarity	NPC477154
0.7849	Intermediate Similarity	NPC117854
0.7849	Intermediate Similarity	NPC218226
0.7845	Intermediate Similarity	NPC227062
0.7845	Intermediate Similarity	NPC142339
0.7845	Intermediate Similarity	NPC274730
0.7842	Intermediate Similarity	NPC207467
0.7841	Intermediate Similarity	NPC225173
0.7841	Intermediate Similarity	NPC163846
0.7841	Intermediate Similarity	NPC237208
0.7838	Intermediate Similarity	NPC239752
0.7838	Intermediate Similarity	NPC275780

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 NPC214901 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	423
0.1-0.2	1124
0.2-0.3	2184
0.3-0.4	2738
0.4-0.5	1599
0.5-0.6	761
0.6-0.7	264
0.7-0.8	57
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
0.8	Intermediate Similarity	NPD5844	Phase 1
0.7923	Intermediate Similarity	NPD6232	Discontinued
0.7796	Intermediate Similarity	NPD7473	Discontinued
0.7647	Intermediate Similarity	NPD2403	Approved
0.7637	Intermediate Similarity	NPD2801	Approved
0.7637	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD2532	Approved
0.7584	Intermediate Similarity	NPD2533	Approved
0.7584	Intermediate Similarity	NPD2534	Approved
0.7582	Intermediate Similarity	NPD1934	Approved
0.7541	Intermediate Similarity	NPD7819	Suspended
0.75	Intermediate Similarity	NPD3817	Phase 2
0.7444	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7433	Intermediate Similarity	NPD5494	Approved
0.7394	Intermediate Similarity	NPD6959	Discontinued
0.738	Intermediate Similarity	NPD919	Approved
0.7366	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7366	Intermediate Similarity	NPD3882	Suspended
0.7363	Intermediate Similarity	NPD2370	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD1465	Phase 2
0.7345	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD7075	Discontinued
0.7302	Intermediate Similarity	NPD1247	Approved
0.7293	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD6599	Discontinued
0.7282	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7277	Intermediate Similarity	NPD6166	Phase 2
0.7277	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7277	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7258	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7243	Intermediate Similarity	NPD7411	Suspended
0.7238	Intermediate Similarity	NPD1511	Approved
0.7236	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD2935	Discontinued
0.7232	Intermediate Similarity	NPD1551	Phase 2
0.7231	Intermediate Similarity	NPD6559	Discontinued
0.7228	Intermediate Similarity	NPD3226	Approved
0.7216	Intermediate Similarity	NPD7074	Phase 3
0.7202	Intermediate Similarity	NPD3818	Discontinued
0.7165	Intermediate Similarity	NPD7054	Approved
0.7158	Intermediate Similarity	NPD1512	Approved
0.7143	Intermediate Similarity	NPD6799	Approved
0.7128	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD7472	Approved
0.7112	Intermediate Similarity	NPD6801	Discontinued
0.7098	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD4380	Phase 2
0.7094	Intermediate Similarity	NPD4360	Phase 2
0.7094	Intermediate Similarity	NPD4363	Phase 3
0.709	Intermediate Similarity	NPD7768	Phase 2
0.7083	Intermediate Similarity	NPD5710	Approved
0.7083	Intermediate Similarity	NPD5711	Approved
0.7027	Intermediate Similarity	NPD920	Approved
0.7021	Intermediate Similarity	NPD37	Approved
0.702	Intermediate Similarity	NPD7808	Phase 3
0.7016	Intermediate Similarity	NPD6234	Discontinued
0.7005	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD6797	Phase 2
0.7	Intermediate Similarity	NPD4967	Phase 2
0.7	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4966	Approved
0.7	Intermediate Similarity	NPD4965	Approved
0.7	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD4628	Phase 3
0.6978	Remote Similarity	NPD3750	Approved
0.6976	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6976	Remote Similarity	NPD4361	Phase 2
0.697	Remote Similarity	NPD7251	Discontinued
0.6966	Remote Similarity	NPD1607	Approved
0.6963	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD3749	Approved
0.6961	Remote Similarity	NPD1549	Phase 2
0.6947	Remote Similarity	NPD5402	Approved
0.6943	Remote Similarity	NPD7199	Phase 2
0.6923	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD1578	Phase 2
0.691	Remote Similarity	NPD447	Suspended
0.6906	Remote Similarity	NPD2346	Discontinued
0.6904	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6902	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD2799	Discontinued
0.6889	Remote Similarity	NPD1510	Phase 2
0.6872	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD1240	Approved
0.6851	Remote Similarity	NPD2796	Approved
0.6842	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6836	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD2800	Approved
0.6831	Remote Similarity	NPD1243	Approved
0.6816	Remote Similarity	NPD230	Phase 1
0.6798	Remote Similarity	NPD8434	Phase 2
0.6796	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6793	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD3926	Phase 2
0.6774	Remote Similarity	NPD7390	Discontinued
0.6768	Remote Similarity	NPD7228	Approved
0.6759	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD7783	Phase 2
0.6755	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.675	Remote Similarity	NPD5953	Discontinued
0.6749	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6738	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6734	Remote Similarity	NPD7286	Phase 2
0.6733	Remote Similarity	NPD8313	Approved
0.6733	Remote Similarity	NPD8312	Approved
0.6703	Remote Similarity	NPD3748	Approved
0.6702	Remote Similarity	NPD958	Approved
0.6684	Remote Similarity	NPD2379	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5403	Approved
0.6667	Remote Similarity	NPD6099	Approved
0.6667	Remote Similarity	NPD6785	Approved
0.6667	Remote Similarity	NPD7435	Discontinued
0.6667	Remote Similarity	NPD2354	Approved
0.6667	Remote Similarity	NPD6784	Approved
0.6667	Remote Similarity	NPD8151	Discontinued
0.6667	Remote Similarity	NPD3887	Approved
0.6667	Remote Similarity	NPD6100	Approved
0.665	Remote Similarity	NPD7229	Phase 3
0.6649	Remote Similarity	NPD4972	Discontinued
0.6634	Remote Similarity	NPD8150	Discontinued
0.6632	Remote Similarity	NPD1653	Approved
0.6632	Remote Similarity	NPD957	Approved
0.6616	Remote Similarity	NPD5242	Approved
0.6613	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD6782	Approved
0.6604	Remote Similarity	NPD6780	Approved
0.6604	Remote Similarity	NPD6778	Approved
0.6604	Remote Similarity	NPD6777	Approved
0.6604	Remote Similarity	NPD6776	Approved
0.6604	Remote Similarity	NPD6779	Approved
0.6604	Remote Similarity	NPD6781	Approved
0.6576	Remote Similarity	NPD5406	Approved
0.6576	Remote Similarity	NPD5404	Approved
0.6576	Remote Similarity	NPD5405	Approved
0.6576	Remote Similarity	NPD5408	Approved
0.6575	Remote Similarity	NPD4060	Phase 1
0.6575	Remote Similarity	NPD943	Approved
0.6573	Remote Similarity	NPD454	Approved
0.6561	Remote Similarity	NPD5401	Approved
0.6561	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6554	Remote Similarity	NPD1203	Approved
0.6541	Remote Similarity	NPD2353	Approved
0.6541	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD1933	Approved
0.6538	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD1184	Approved
0.6536	Remote Similarity	NPD6832	Phase 2
0.6522	Remote Similarity	NPD651	Clinical (unspecified phase)
0.652	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD7177	Discontinued
0.6517	Remote Similarity	NPD3751	Discontinued
0.6515	Remote Similarity	NPD8127	Discontinued
0.6512	Remote Similarity	NPD7697	Approved
0.6512	Remote Similarity	NPD7696	Phase 3
0.6512	Remote Similarity	NPD7698	Approved
0.651	Remote Similarity	NPD7458	Discontinued
0.6505	Remote Similarity	NPD4534	Discontinued
0.6503	Remote Similarity	NPD6651	Approved
0.65	Remote Similarity	NPD3027	Phase 3
0.65	Remote Similarity	NPD4625	Phase 3
0.6486	Remote Similarity	NPD4476	Approved
0.6486	Remote Similarity	NPD4477	Approved
0.6484	Remote Similarity	NPD7874	Approved
0.6484	Remote Similarity	NPD1613	Approved
0.6484	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6482	Remote Similarity	NPD3787	Discontinued
0.6481	Remote Similarity	NPD7870	Phase 2
0.6481	Remote Similarity	NPD7871	Phase 2
0.648	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD7240	Approved
0.6467	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD4538	Approved
0.6467	Remote Similarity	NPD4536	Approved
0.6464	Remote Similarity	NPD411	Approved
0.6464	Remote Similarity	NPD2313	Discontinued
0.6464	Remote Similarity	NPD3268	Approved
0.6445	Remote Similarity	NPD6312	Discontinued
0.6444	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.644	Remote Similarity	NPD6273	Approved
0.6439	Remote Similarity	NPD7549	Discontinued
0.6436	Remote Similarity	NPD7003	Approved
0.6432	Remote Similarity	NPD4308	Phase 3
0.6429	Remote Similarity	NPD5353	Approved
0.6417	Remote Similarity	NPD5958	Discontinued
0.6404	Remote Similarity	NPD1283	Approved
0.6402	Remote Similarity	NPD6190	Approved
0.6398	Remote Similarity	NPD2438	Suspended
0.6393	Remote Similarity	NPD7701	Phase 2
0.6393	Remote Similarity	NPD2979	Phase 3
0.639	Remote Similarity	NPD7039	Approved
0.639	Remote Similarity	NPD7038	Approved
0.639	Remote Similarity	NPD3303	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