NPASS Compound

Structure

NPC27999 OpenBabel07101718312D 26 29 0 0 1 0 0 0 0 0999 V2000 -1.8254 -2.3079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4319 2.5910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8517 1.7136 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8618 -2.3079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3436 -1.4733 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1360 -0.5759 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1649 0.3873 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2875 -1.0325 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3800 -0.7795 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2209 -1.8203 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5428 -0.7962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2209 -0.4325 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8218 -1.4733 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.1175 0.2536 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3451 0.8939 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3800 -1.4733 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4678 -0.5259 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8218 -0.7795 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5895 0.7623 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4966 0.4372 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6564 -1.9552 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8033 0.5377 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4037 0.0887 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6822 1.7214 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9147 1.3054 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 5 2 0 0 0 0 2 15 1 0 0 0 0 3 15 1 0 0 0 0 5 16 1 0 0 0 0 6 7 1 0 0 0 0 6 8 1 0 0 0 0 7 15 1 0 0 0 0 8 17 1 0 0 0 0 9 12 2 0 0 0 0 9 16 1 0 0 0 0 10 13 1 0 0 0 0 10 16 1 0 0 0 0 11 17 1 0 0 0 0 11 26 1 0 0 0 0 12 14 1 0 0 0 0 12 18 1 0 0 0 0 13 18 1 6 0 0 0 13 21 1 0 0 0 0 14 19 1 0 0 0 0 14 22 2 0 0 0 0 15 20 1 0 0 0 0 16 4 1 1 0 0 0 17 18 1 6 0 0 0 18 23 1 6 0 0 0 19 20 1 6 0 0 0 19 24 1 0 0 0 0 19 26 1 0 0 0 0 20 17 1 6 0 0 0 20 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	364.19
Volume:	365.082
LogP:	1.896
LogD:	1.353
LogS:	-3.864
# Rotatable Bonds:	1
TPSA:	107.22
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.514
Synthetic Accessibility Score:	6.209
Fsp3:	0.75
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:	-5.122
MDCK Permeability:	2.0665645934059285e-05
Pgp-inhibitor:	0.009
Pgp-substrate:	0.322
Human Intestinal Absorption (HIA):	0.045
20% Bioavailability (F20%):	0.221
30% Bioavailability (F30%):	0.02

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.972
Plasma Protein Binding (PPB):	77.5610122680664%
Volume Distribution (VD):	1.262
Pgp-substrate:	28.826448440551758%

ADMET: Metabolism

CYP1A2-inhibitor:	0.013
CYP1A2-substrate:	0.979
CYP2C19-inhibitor:	0.033
CYP2C19-substrate:	0.803
CYP2C9-inhibitor:	0.162
CYP2C9-substrate:	0.005
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.038
CYP3A4-inhibitor:	0.706
CYP3A4-substrate:	0.901

ADMET: Excretion

Clearance (CL):	1.689
Half-life (T1/2):	0.176

ADMET: Toxicity

hERG Blockers:	0.017
Human Hepatotoxicity (H-HT):	0.701
Drug-inuced Liver Injury (DILI):	0.162
AMES Toxicity:	0.635
Rat Oral Acute Toxicity:	0.583
Maximum Recommended Daily Dose:	0.909
Skin Sensitization:	0.396
Carcinogencity:	0.989
Eye Corrosion:	0.003
Eye Irritation:	0.062
Respiratory Toxicity:	0.975

Download Data

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

Natural Product: NPC27999

Natural Product ID:	NPC27999
*Common Name:**	Diaporthins B
IUPAC Name:	n.a.
Synonyms:	Diaporthins B
Standard InCHIKey:	FVYIOIBMUVNZMQ-KNHLKMAJSA-N
Standard InCHI:	InChI=1S/C20H28O6/c1-5-16(4)9-12-14(22)19(24)20(25)15(2,3)7-6-8-17(20,11-26-19)18(12,23)13(21)10-16/h5,9,13,21,23-25H,1,6-8,10-11H2,2-4H3/t13-,16-,17+,18+,19-,20-/m1/s1
SMILES:	C=C[C@@]1(C)C[C@@H](O)[C@]2(C(=C1)C(=O)[C@@]1([C@@]3([C@@]2(CCCC3(C)C)CO1)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2017495
PubChem CID:	70695904
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001729] Oxepanes

*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
NPO33396	Epicoccum sp. HS-1	Species	Didymellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22418279]

☑ 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	2

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	=	3.86	ug.mL-1	PMID[451686]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	6.52	ug.mL-1	PMID[451686]

☑ 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 NPC27999 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	242
0.1-0.2	1399
0.2-0.3	4160
0.3-0.4	7138
0.4-0.5	10986
0.5-0.6	10325
0.6-0.7	5951
0.7-0.8	2277
0.8-0.85	188
0.85-0.9	26
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC477116
0.9304	High Similarity	NPC225049
0.9286	High Similarity	NPC268958
0.887	High Similarity	NPC112038
0.8783	High Similarity	NPC469488
0.8761	High Similarity	NPC261330
0.875	High Similarity	NPC472002
0.8729	High Similarity	NPC470922
0.8696	High Similarity	NPC204552
0.8696	High Similarity	NPC188667
0.8696	High Similarity	NPC251310
0.8684	High Similarity	NPC179626
0.8649	High Similarity	NPC20192
0.8632	High Similarity	NPC477046
0.8632	High Similarity	NPC102822
0.8621	High Similarity	NPC470777
0.8609	High Similarity	NPC470854
0.8609	High Similarity	NPC176513
0.8609	High Similarity	NPC287343
0.8609	High Similarity	NPC97908
0.8609	High Similarity	NPC474654
0.8609	High Similarity	NPC122033
0.8609	High Similarity	NPC470775
0.8571	High Similarity	NPC24651
0.8547	High Similarity	NPC478051
0.8534	High Similarity	NPC297179
0.8534	High Similarity	NPC470776
0.8534	High Similarity	NPC17772
0.8522	High Similarity	NPC207217
0.8509	High Similarity	NPC51978
0.8487	Intermediate Similarity	NPC67251
0.8482	Intermediate Similarity	NPC220705
0.8455	Intermediate Similarity	NPC102316
0.8435	Intermediate Similarity	NPC117712
0.8421	Intermediate Similarity	NPC269530
0.8417	Intermediate Similarity	NPC476729
0.8407	Intermediate Similarity	NPC474567
0.8403	Intermediate Similarity	NPC312833
0.839	Intermediate Similarity	NPC107338
0.839	Intermediate Similarity	NPC109607
0.8387	Intermediate Similarity	NPC168879
0.8362	Intermediate Similarity	NPC134869
0.8362	Intermediate Similarity	NPC474734
0.8362	Intermediate Similarity	NPC474046
0.8362	Intermediate Similarity	NPC96312
0.8362	Intermediate Similarity	NPC328374
0.8362	Intermediate Similarity	NPC40632
0.8362	Intermediate Similarity	NPC259306
0.8362	Intermediate Similarity	NPC470628
0.8362	Intermediate Similarity	NPC152199
0.8362	Intermediate Similarity	NPC235539
0.8362	Intermediate Similarity	NPC251236
0.8349	Intermediate Similarity	NPC470184
0.8348	Intermediate Similarity	NPC49451
0.8348	Intermediate Similarity	NPC198539
0.8348	Intermediate Similarity	NPC7921
0.8348	Intermediate Similarity	NPC208998
0.8333	Intermediate Similarity	NPC243014
0.8333	Intermediate Similarity	NPC171888
0.8333	Intermediate Similarity	NPC265557
0.8333	Intermediate Similarity	NPC18945
0.8333	Intermediate Similarity	NPC105926
0.8333	Intermediate Similarity	NPC201992
0.8333	Intermediate Similarity	NPC91693
0.8333	Intermediate Similarity	NPC471243
0.8333	Intermediate Similarity	NPC146945
0.8319	Intermediate Similarity	NPC141350
0.8319	Intermediate Similarity	NPC87335
0.8305	Intermediate Similarity	NPC476529
0.8305	Intermediate Similarity	NPC475775
0.8304	Intermediate Similarity	NPC144854
0.8304	Intermediate Similarity	NPC3316
0.8291	Intermediate Similarity	NPC218970
0.8291	Intermediate Similarity	NPC469684
0.8276	Intermediate Similarity	NPC268238
0.8276	Intermediate Similarity	NPC18547
0.8276	Intermediate Similarity	NPC469877
0.8276	Intermediate Similarity	NPC143268
0.8276	Intermediate Similarity	NPC473798
0.8276	Intermediate Similarity	NPC45218
0.8276	Intermediate Similarity	NPC323821
0.8276	Intermediate Similarity	NPC474906
0.8276	Intermediate Similarity	NPC470919
0.8276	Intermediate Similarity	NPC80650
0.8261	Intermediate Similarity	NPC90769
0.8261	Intermediate Similarity	NPC474516
0.8261	Intermediate Similarity	NPC289312
0.8261	Intermediate Similarity	NPC302146
0.8261	Intermediate Similarity	NPC11252
0.825	Intermediate Similarity	NPC222688
0.8246	Intermediate Similarity	NPC5103
0.823	Intermediate Similarity	NPC277017
0.823	Intermediate Similarity	NPC192813
0.823	Intermediate Similarity	NPC154608
0.822	Intermediate Similarity	NPC240509
0.822	Intermediate Similarity	NPC21326
0.8205	Intermediate Similarity	NPC16081
0.8205	Intermediate Similarity	NPC173686
0.8197	Intermediate Similarity	NPC293112
0.819	Intermediate Similarity	NPC477266
0.8174	Intermediate Similarity	NPC474229
0.8167	Intermediate Similarity	NPC470779
0.816	Intermediate Similarity	NPC254614
0.816	Intermediate Similarity	NPC100390
0.8158	Intermediate Similarity	NPC143706
0.8158	Intermediate Similarity	NPC472534
0.8142	Intermediate Similarity	NPC230541
0.8136	Intermediate Similarity	NPC13713
0.8136	Intermediate Similarity	NPC58662
0.8136	Intermediate Similarity	NPC473590
0.8136	Intermediate Similarity	NPC473968
0.813	Intermediate Similarity	NPC470780
0.813	Intermediate Similarity	NPC470882
0.8125	Intermediate Similarity	NPC295885
0.8125	Intermediate Similarity	NPC596
0.8125	Intermediate Similarity	NPC140045
0.812	Intermediate Similarity	NPC243354
0.812	Intermediate Similarity	NPC247069
0.8115	Intermediate Similarity	NPC81736
0.8115	Intermediate Similarity	NPC172154
0.8103	Intermediate Similarity	NPC205534
0.8099	Intermediate Similarity	NPC313528
0.8087	Intermediate Similarity	NPC235014
0.8087	Intermediate Similarity	NPC46407
0.8083	Intermediate Similarity	NPC48692
0.808	Intermediate Similarity	NPC476863
0.808	Intermediate Similarity	NPC476862
0.808	Intermediate Similarity	NPC476852
0.8067	Intermediate Similarity	NPC284707
0.8067	Intermediate Similarity	NPC478205
0.8067	Intermediate Similarity	NPC478206
0.8067	Intermediate Similarity	NPC108581
0.8065	Intermediate Similarity	NPC475636
0.8065	Intermediate Similarity	NPC476859
0.8065	Intermediate Similarity	NPC295220
0.8053	Intermediate Similarity	NPC181357
0.8053	Intermediate Similarity	NPC472645
0.8053	Intermediate Similarity	NPC102352
0.8051	Intermediate Similarity	NPC270478
0.8051	Intermediate Similarity	NPC478216
0.8049	Intermediate Similarity	NPC477745
0.8047	Intermediate Similarity	NPC141215
0.8047	Intermediate Similarity	NPC190065
0.8047	Intermediate Similarity	NPC251998
0.8047	Intermediate Similarity	NPC471089
0.8034	Intermediate Similarity	NPC478212
0.8034	Intermediate Similarity	NPC194273
0.8034	Intermediate Similarity	NPC469454
0.8034	Intermediate Similarity	NPC108721
0.8034	Intermediate Similarity	NPC469463
0.8034	Intermediate Similarity	NPC73300
0.8034	Intermediate Similarity	NPC25909
0.8034	Intermediate Similarity	NPC469496
0.8033	Intermediate Similarity	NPC11895
0.8033	Intermediate Similarity	NPC227397
0.8033	Intermediate Similarity	NPC469789
0.8031	Intermediate Similarity	NPC242486
0.8031	Intermediate Similarity	NPC15215
0.8017	Intermediate Similarity	NPC469655
0.8017	Intermediate Similarity	NPC304180
0.8017	Intermediate Similarity	NPC179798
0.8017	Intermediate Similarity	NPC474846
0.8017	Intermediate Similarity	NPC188738
0.8017	Intermediate Similarity	NPC469656
0.8017	Intermediate Similarity	NPC472401
0.8017	Intermediate Similarity	NPC157476
0.8017	Intermediate Similarity	NPC476023
0.8016	Intermediate Similarity	NPC33378
0.8016	Intermediate Similarity	NPC254146
0.8016	Intermediate Similarity	NPC6274
0.8	Intermediate Similarity	NPC231529
0.8	Intermediate Similarity	NPC264192
0.8	Intermediate Similarity	NPC473920
0.8	Intermediate Similarity	NPC476107
0.8	Intermediate Similarity	NPC476851
0.8	Intermediate Similarity	NPC309096
0.8	Intermediate Similarity	NPC279143
0.8	Intermediate Similarity	NPC162495
0.8	Intermediate Similarity	NPC54614
0.7984	Intermediate Similarity	NPC473265
0.7984	Intermediate Similarity	NPC476008
0.7984	Intermediate Similarity	NPC473253
0.7983	Intermediate Similarity	NPC98249
0.7983	Intermediate Similarity	NPC478204
0.7983	Intermediate Similarity	NPC156252
0.7983	Intermediate Similarity	NPC53396
0.7969	Intermediate Similarity	NPC262813
0.7967	Intermediate Similarity	NPC8369
0.7966	Intermediate Similarity	NPC326542
0.7966	Intermediate Similarity	NPC299849
0.7965	Intermediate Similarity	NPC296950
0.7965	Intermediate Similarity	NPC146731
0.7953	Intermediate Similarity	NPC478151
0.7951	Intermediate Similarity	NPC19464
0.7951	Intermediate Similarity	NPC170538
0.7949	Intermediate Similarity	NPC207251
0.7937	Intermediate Similarity	NPC475606
0.7937	Intermediate Similarity	NPC476855
0.7937	Intermediate Similarity	NPC477189
0.7937	Intermediate Similarity	NPC475314

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 NPC27999 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	207
0.1-0.2	1640
0.2-0.3	3732
0.3-0.4	2311
0.4-0.5	702
0.5-0.6	319
0.6-0.7	152
0.7-0.8	81
0.8-0.85	6
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8235	Intermediate Similarity	NPD6054	Approved
0.8167	Intermediate Similarity	NPD6016	Approved
0.8167	Intermediate Similarity	NPD6015	Approved
0.8099	Intermediate Similarity	NPD5988	Approved
0.8099	Intermediate Similarity	NPD6370	Approved
0.7967	Intermediate Similarity	NPD7492	Approved
0.7934	Intermediate Similarity	NPD6059	Approved
0.7934	Intermediate Similarity	NPD6319	Approved
0.7913	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7903	Intermediate Similarity	NPD6616	Approved
0.784	Intermediate Similarity	NPD7078	Approved
0.7778	Intermediate Similarity	NPD7736	Approved
0.7686	Intermediate Similarity	NPD6009	Approved
0.7627	Intermediate Similarity	NPD4634	Approved
0.76	Intermediate Similarity	NPD8328	Phase 3
0.7583	Intermediate Similarity	NPD4632	Approved
0.7559	Intermediate Similarity	NPD8293	Discontinued
0.7542	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7541	Intermediate Similarity	NPD7115	Discovery
0.7522	Intermediate Similarity	NPD4225	Approved
0.7521	Intermediate Similarity	NPD5697	Approved
0.75	Intermediate Similarity	NPD8297	Approved
0.75	Intermediate Similarity	NPD6882	Approved
0.7478	Intermediate Similarity	NPD5211	Phase 2
0.7458	Intermediate Similarity	NPD6899	Approved
0.7458	Intermediate Similarity	NPD6881	Approved
0.7417	Intermediate Similarity	NPD6650	Approved
0.7417	Intermediate Similarity	NPD6649	Approved
0.7398	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7395	Intermediate Similarity	NPD6012	Approved
0.7395	Intermediate Similarity	NPD6014	Approved
0.7395	Intermediate Similarity	NPD6013	Approved
0.7364	Intermediate Similarity	NPD6033	Approved
0.735	Intermediate Similarity	NPD5141	Approved
0.7333	Intermediate Similarity	NPD6883	Approved
0.7333	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7290	Approved
0.7333	Intermediate Similarity	NPD7102	Approved
0.7311	Intermediate Similarity	NPD6011	Approved
0.7304	Intermediate Similarity	NPD4696	Approved
0.7304	Intermediate Similarity	NPD5285	Approved
0.7304	Intermediate Similarity	NPD5286	Approved
0.7302	Intermediate Similarity	NPD5983	Phase 2
0.7288	Intermediate Similarity	NPD6675	Approved
0.7288	Intermediate Similarity	NPD7128	Approved
0.7288	Intermediate Similarity	NPD5739	Approved
0.7288	Intermediate Similarity	NPD6402	Approved
0.7273	Intermediate Similarity	NPD6617	Approved
0.7273	Intermediate Similarity	NPD6869	Approved
0.7273	Intermediate Similarity	NPD6847	Approved
0.7273	Intermediate Similarity	NPD8130	Phase 1
0.725	Intermediate Similarity	NPD6372	Approved
0.725	Intermediate Similarity	NPD6373	Approved
0.7227	Intermediate Similarity	NPD5701	Approved
0.7188	Intermediate Similarity	NPD7604	Phase 2
0.7179	Intermediate Similarity	NPD4633	Approved
0.7179	Intermediate Similarity	NPD5226	Approved
0.7179	Intermediate Similarity	NPD5225	Approved
0.7179	Intermediate Similarity	NPD5224	Approved
0.7176	Intermediate Similarity	NPD7319	Approved
0.7167	Intermediate Similarity	NPD7320	Approved
0.7167	Intermediate Similarity	NPD6686	Approved
0.7165	Intermediate Similarity	NPD6921	Approved
0.713	Intermediate Similarity	NPD4755	Approved
0.7119	Intermediate Similarity	NPD5174	Approved
0.7119	Intermediate Similarity	NPD5175	Approved
0.7094	Intermediate Similarity	NPD5223	Approved
0.7083	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD6412	Phase 2
0.7077	Intermediate Similarity	NPD6336	Discontinued
0.7043	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD5222	Approved
0.7043	Intermediate Similarity	NPD5221	Approved
0.7031	Intermediate Similarity	NPD8516	Approved
0.7031	Intermediate Similarity	NPD8517	Approved
0.7031	Intermediate Similarity	NPD8515	Approved
0.7031	Intermediate Similarity	NPD8513	Phase 3
0.7018	Intermediate Similarity	NPD5282	Discontinued
0.7009	Intermediate Similarity	NPD4700	Approved
0.7	Intermediate Similarity	NPD6008	Approved
0.6992	Remote Similarity	NPD5956	Approved
0.6983	Remote Similarity	NPD5173	Approved
0.6967	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD5344	Discontinued
0.6947	Remote Similarity	NPD7507	Approved
0.6905	Remote Similarity	NPD6274	Approved
0.6897	Remote Similarity	NPD4697	Phase 3
0.6885	Remote Similarity	NPD4729	Approved
0.6885	Remote Similarity	NPD4730	Approved
0.6875	Remote Similarity	NPD7100	Approved
0.6875	Remote Similarity	NPD7101	Approved
0.6855	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.685	Remote Similarity	NPD6317	Approved
0.6842	Remote Similarity	NPD6079	Approved
0.6797	Remote Similarity	NPD6313	Approved
0.6797	Remote Similarity	NPD6335	Approved
0.6797	Remote Similarity	NPD6314	Approved
0.6783	Remote Similarity	NPD5779	Approved
0.6783	Remote Similarity	NPD5778	Approved
0.6774	Remote Similarity	NPD5247	Approved
0.6774	Remote Similarity	NPD6371	Approved
0.6774	Remote Similarity	NPD5248	Approved
0.6774	Remote Similarity	NPD5250	Approved
0.6774	Remote Similarity	NPD5251	Approved
0.6774	Remote Similarity	NPD5249	Phase 3
0.6769	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6767	Remote Similarity	NPD8074	Phase 3
0.6748	Remote Similarity	NPD5128	Approved
0.6744	Remote Similarity	NPD7516	Approved
0.6723	Remote Similarity	NPD7640	Approved
0.6723	Remote Similarity	NPD7639	Approved
0.6721	Remote Similarity	NPD4768	Approved
0.6721	Remote Similarity	NPD4767	Approved
0.672	Remote Similarity	NPD5217	Approved
0.672	Remote Similarity	NPD5216	Approved
0.672	Remote Similarity	NPD5215	Approved
0.672	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD3618	Phase 1
0.6696	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD6083	Phase 2
0.6695	Remote Similarity	NPD6084	Phase 2
0.6694	Remote Similarity	NPD4754	Approved
0.6667	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5210	Approved
0.6667	Remote Similarity	NPD4629	Approved
0.6667	Remote Similarity	NPD5328	Approved
0.6667	Remote Similarity	NPD7328	Approved
0.6667	Remote Similarity	NPD7327	Approved
0.6641	Remote Similarity	NPD6868	Approved
0.664	Remote Similarity	NPD5135	Approved
0.664	Remote Similarity	NPD5169	Approved
0.664	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD7638	Approved
0.6639	Remote Similarity	NPD5696	Approved
0.6587	Remote Similarity	NPD5127	Approved
0.6583	Remote Similarity	NPD6648	Approved
0.6555	Remote Similarity	NPD7902	Approved
0.6552	Remote Similarity	NPD7983	Approved
0.6552	Remote Similarity	NPD6411	Approved
0.6541	Remote Similarity	NPD6067	Discontinued
0.6525	Remote Similarity	NPD5695	Phase 3
0.6522	Remote Similarity	NPD4753	Phase 2
0.6515	Remote Similarity	NPD6908	Approved
0.6515	Remote Similarity	NPD6909	Approved
0.6515	Remote Similarity	NPD7503	Approved
0.6496	Remote Similarity	NPD6399	Phase 3
0.6496	Remote Similarity	NPD4202	Approved
0.6491	Remote Similarity	NPD3573	Approved
0.6489	Remote Similarity	NPD4522	Approved
0.648	Remote Similarity	NPD5168	Approved
0.646	Remote Similarity	NPD1694	Approved
0.646	Remote Similarity	NPD1696	Phase 3
0.6455	Remote Similarity	NPD4695	Discontinued
0.6454	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6449	Remote Similarity	NPD7260	Phase 2
0.6441	Remote Similarity	NPD7748	Approved
0.6434	Remote Similarity	NPD5167	Approved
0.6429	Remote Similarity	NPD6110	Phase 1
0.6424	Remote Similarity	NPD8407	Phase 2
0.641	Remote Similarity	NPD7515	Phase 2
0.641	Remote Similarity	NPD7637	Suspended
0.6408	Remote Similarity	NPD6333	Approved
0.6408	Remote Similarity	NPD6334	Approved
0.6393	Remote Similarity	NPD1700	Approved
0.6391	Remote Similarity	NPD8378	Approved
0.6391	Remote Similarity	NPD8296	Approved
0.6391	Remote Similarity	NPD8379	Approved
0.6391	Remote Similarity	NPD8380	Approved
0.6391	Remote Similarity	NPD8335	Approved
0.6391	Remote Similarity	NPD8033	Approved
0.6379	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6379	Remote Similarity	NPD6101	Approved
0.6348	Remote Similarity	NPD7524	Approved
0.6341	Remote Similarity	NPD7632	Discontinued
0.6341	Remote Similarity	NPD8368	Discontinued
0.6339	Remote Similarity	NPD3667	Approved
0.6316	Remote Similarity	NPD8294	Approved
0.6316	Remote Similarity	NPD8377	Approved
0.6303	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD7900	Approved
0.6293	Remote Similarity	NPD6672	Approved
0.6293	Remote Similarity	NPD5737	Approved
0.6286	Remote Similarity	NPD6845	Suspended
0.6279	Remote Similarity	NPD6053	Discontinued
0.6261	Remote Similarity	NPD5279	Phase 3
0.6261	Remote Similarity	NPD4519	Discontinued
0.6261	Remote Similarity	NPD4623	Approved
0.6231	Remote Similarity	NPD8133	Approved
0.623	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6228	Remote Similarity	NPD4786	Approved
0.6228	Remote Similarity	NPD3666	Approved
0.6228	Remote Similarity	NPD3665	Phase 1
0.6228	Remote Similarity	NPD3133	Approved
0.6196	Remote Similarity	NPD7799	Discontinued
0.6186	Remote Similarity	NPD6698	Approved
0.6186	Remote Similarity	NPD46	Approved
0.6186	Remote Similarity	NPD5785	Approved
0.6154	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD8434	Phase 2

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data