NPASS Compound

Structure

CID107283 OpenBabel06191715452D 23 25 0 0 1 0 0 0 0 0999 V2000 -0.5878 2.5411 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 3.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4122 -0.9230 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0878 1.6750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0878 -0.0570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0878 1.6750 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0878 -0.0570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 0.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8171 -1.1910 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 -3.5878 0.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -0.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 2.5691 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 2.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 -0.9230 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 7 1 0 0 0 0 2 21 1 0 0 0 0 3 22 1 0 0 0 0 4 7 1 0 0 0 0 4 8 1 0 0 0 0 5 8 1 0 0 0 0 5 11 2 0 0 0 0 6 9 2 0 0 0 0 6 10 1 0 0 0 0 7 16 1 1 0 0 0 8 18 2 0 0 0 0 9 13 1 0 0 0 0 9 19 1 0 0 0 0 10 12 2 0 0 0 0 10 21 1 0 0 0 0 11 22 1 0 0 0 0 12 14 1 0 0 0 0 12 15 1 0 0 0 0 13 14 2 0 0 0 0 13 17 1 0 0 0 0 14 23 1 0 0 0 0 15 16 1 0 0 0 0 15 20 2 0 0 0 0 16 11 1 1 0 0 0 16 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	151.06
Volume:	156.399
LogP:	1.177
LogD:	1.293
LogS:	-0.623
# Rotatable Bonds:	3
TPSA:	39.19
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	1
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.597
Synthetic Accessibility Score:	1.573
Fsp3:	0.25
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.144
MDCK Permeability:	3.7176469049882144e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.32
30% Bioavailability (F30%):	0.913

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.936
Plasma Protein Binding (PPB):	55.344871520996094%
Volume Distribution (VD):	1.332
Pgp-substrate:	44.043617248535156%

ADMET: Metabolism

CYP1A2-inhibitor:	0.964
CYP1A2-substrate:	0.542
CYP2C19-inhibitor:	0.522
CYP2C19-substrate:	0.463
CYP2C9-inhibitor:	0.086
CYP2C9-substrate:	0.291
CYP2D6-inhibitor:	0.117
CYP2D6-substrate:	0.249
CYP3A4-inhibitor:	0.203
CYP3A4-substrate:	0.263

ADMET: Excretion

Clearance (CL):	12.229
Half-life (T1/2):	0.811

ADMET: Toxicity

hERG Blockers:	0.057
Human Hepatotoxicity (H-HT):	0.011
Drug-inuced Liver Injury (DILI):	0.88
AMES Toxicity:	0.013
Rat Oral Acute Toxicity:	0.098
Maximum Recommended Daily Dose:	0.014
Skin Sensitization:	0.766
Carcinogencity:	0.165
Eye Corrosion:	0.033
Eye Irritation:	0.987
Respiratory Toxicity:	0.069

Download Data

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

Natural Product: NPC107283

Natural Product ID:	NPC107283
*Common Name:**	(2S,5'r)-7-Chloro-6-Hydroxy-3',4-Dimethoxy-5'-Methylspiro[1-Benzofuran-2,4'-Cyclohex-2-Ene]-1',3-Dione
IUPAC Name:	(2S,5'R)-7-chloro-6-hydroxy-3',4-dimethoxy-5'-methylspiro[1-benzofuran-2,4'-cyclohex-2-ene]-1',3-dione
Synonyms:
Standard InCHIKey:	SYNGDIBHUPXIQA-QZTNRIJFSA-N
Standard InCHI:	InChI=1S/C16H15ClO6/c1-7-4-8(18)5-11(22-3)16(7)15(20)12-10(21-2)6-9(19)13(17)14(12)23-16/h5-7,19H,4H2,1-3H3/t7-,16+/m1/s1
SMILES:	COC1=CC(=O)C[C@H]([C@@]21Oc1c(C2=O)c(OC)cc(c1Cl)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1956348
PubChem CID:	9974417
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000301] Benzofurans

*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
NPO8752	Xylaria cubensis	Species	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28802670]
NPO6825	Clethra barbinervis	Species	Clethraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO556	Hypericum attenuatum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8752	Xylaria cubensis	Species	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4553	Oxycorynia fascicularis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO5580	Alstonia glaucescens	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4265	Trichocereus pachanoi	Species	Cactaceae	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	2

Activity Type	# Activity
Cell Line	1
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT82	Cell Line	MDA-MB-231	Homo sapiens	Inhibition	<	50.0	%	PMID[494253]
NPT327	Organism	Microsporum gypseum	Microsporum gypseum	IZ	=	0.0	mm	PMID[494254]

☑ 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 NPC107283 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	458
0.1-0.2	2091
0.2-0.3	5613
0.3-0.4	12040
0.4-0.5	6294
0.5-0.6	5721
0.6-0.7	6241
0.7-0.8	4187
0.8-0.85	45
0.85-0.9	3
0.9-0.95	1
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9625	High Similarity	NPC234053
0.843	Intermediate Similarity	NPC148480
0.8256	Intermediate Similarity	NPC68850
0.8239	Intermediate Similarity	NPC477568
0.8235	Intermediate Similarity	NPC475107
0.8235	Intermediate Similarity	NPC43490
0.8208	Intermediate Similarity	NPC62444
0.8198	Intermediate Similarity	NPC476931
0.8161	Intermediate Similarity	NPC472032
0.814	Intermediate Similarity	NPC94796
0.8118	Intermediate Similarity	NPC476930
0.8103	Intermediate Similarity	NPC476255
0.8098	Intermediate Similarity	NPC221185
0.8098	Intermediate Similarity	NPC200207
0.8087	Intermediate Similarity	NPC470100
0.807	Intermediate Similarity	NPC125969
0.8059	Intermediate Similarity	NPC313922
0.8057	Intermediate Similarity	NPC193222
0.8054	Intermediate Similarity	NPC247104
0.8035	Intermediate Similarity	NPC474096
0.8024	Intermediate Similarity	NPC277032
0.8023	Intermediate Similarity	NPC474857
0.8	Intermediate Similarity	NPC471801
0.8	Intermediate Similarity	NPC476056
0.7989	Intermediate Similarity	NPC45072
0.7989	Intermediate Similarity	NPC470081
0.7989	Intermediate Similarity	NPC470099
0.7988	Intermediate Similarity	NPC275878
0.7979	Intermediate Similarity	NPC154720
0.7978	Intermediate Similarity	NPC474499
0.7978	Intermediate Similarity	NPC470422
0.7978	Intermediate Similarity	NPC475080
0.7977	Intermediate Similarity	NPC476929
0.7976	Intermediate Similarity	NPC267117
0.7966	Intermediate Similarity	NPC277865
0.7944	Intermediate Similarity	NPC471802
0.7933	Intermediate Similarity	NPC264922
0.7929	Intermediate Similarity	NPC471229
0.7921	Intermediate Similarity	NPC118128
0.7919	Intermediate Similarity	NPC286422
0.7917	Intermediate Similarity	NPC198927
0.7914	Intermediate Similarity	NPC48822
0.7903	Intermediate Similarity	NPC220369
0.7892	Intermediate Similarity	NPC316535
0.7892	Intermediate Similarity	NPC121100
0.7892	Intermediate Similarity	NPC39409
0.7892	Intermediate Similarity	NPC71210
0.7882	Intermediate Similarity	NPC210597
0.7874	Intermediate Similarity	NPC298401
0.7874	Intermediate Similarity	NPC472405
0.787	Intermediate Similarity	NPC475717
0.787	Intermediate Similarity	NPC116822
0.7869	Intermediate Similarity	NPC99937
0.7865	Intermediate Similarity	NPC470562
0.7865	Intermediate Similarity	NPC470565
0.7861	Intermediate Similarity	NPC214901
0.7849	Intermediate Similarity	NPC471806
0.7849	Intermediate Similarity	NPC471810
0.7845	Intermediate Similarity	NPC472606
0.7842	Intermediate Similarity	NPC108744
0.7841	Intermediate Similarity	NPC173352
0.7841	Intermediate Similarity	NPC58653
0.7838	Intermediate Similarity	NPC471804
0.7838	Intermediate Similarity	NPC471812
0.7838	Intermediate Similarity	NPC471803
0.7836	Intermediate Similarity	NPC203080
0.7836	Intermediate Similarity	NPC209760
0.7836	Intermediate Similarity	NPC100134
0.7831	Intermediate Similarity	NPC113770
0.7829	Intermediate Similarity	NPC219861
0.7829	Intermediate Similarity	NPC245122
0.7829	Intermediate Similarity	NPC473696
0.7821	Intermediate Similarity	NPC470560
0.7821	Intermediate Similarity	NPC188618
0.7818	Intermediate Similarity	NPC111201
0.7803	Intermediate Similarity	NPC161650
0.7803	Intermediate Similarity	NPC472404
0.7798	Intermediate Similarity	NPC202494
0.7798	Intermediate Similarity	NPC47388
0.7798	Intermediate Similarity	NPC473133
0.7798	Intermediate Similarity	NPC472918
0.7798	Intermediate Similarity	NPC470670
0.7797	Intermediate Similarity	NPC28669
0.7796	Intermediate Similarity	NPC471813
0.7796	Intermediate Similarity	NPC471805
0.7791	Intermediate Similarity	NPC476169
0.7791	Intermediate Similarity	NPC471116
0.779	Intermediate Similarity	NPC108278
0.7784	Intermediate Similarity	NPC212697
0.7784	Intermediate Similarity	NPC184649
0.7784	Intermediate Similarity	NPC297788
0.7784	Intermediate Similarity	NPC109180
0.7784	Intermediate Similarity	NPC131578
0.7784	Intermediate Similarity	NPC470857
0.7784	Intermediate Similarity	NPC472581
0.7784	Intermediate Similarity	NPC311144
0.7784	Intermediate Similarity	NPC303185
0.7778	Intermediate Similarity	NPC30550
0.7778	Intermediate Similarity	NPC288534
0.7778	Intermediate Similarity	NPC304954
0.7771	Intermediate Similarity	NPC117985
0.7771	Intermediate Similarity	NPC162476
0.7765	Intermediate Similarity	NPC28042
0.7765	Intermediate Similarity	NPC472421
0.7759	Intermediate Similarity	NPC55738
0.7759	Intermediate Similarity	NPC264932
0.7759	Intermediate Similarity	NPC311574
0.7759	Intermediate Similarity	NPC195832
0.7758	Intermediate Similarity	NPC103342
0.7758	Intermediate Similarity	NPC230285
0.7758	Intermediate Similarity	NPC103904
0.7758	Intermediate Similarity	NPC59951
0.7758	Intermediate Similarity	NPC146679
0.7758	Intermediate Similarity	NPC82920
0.7758	Intermediate Similarity	NPC164697
0.7758	Intermediate Similarity	NPC184536
0.7758	Intermediate Similarity	NPC477272
0.7758	Intermediate Similarity	NPC289660
0.7754	Intermediate Similarity	NPC471807
0.7753	Intermediate Similarity	NPC223413
0.7753	Intermediate Similarity	NPC95715
0.7751	Intermediate Similarity	NPC470460
0.7751	Intermediate Similarity	NPC211811
0.7747	Intermediate Similarity	NPC28160
0.7746	Intermediate Similarity	NPC146636
0.7746	Intermediate Similarity	NPC164427
0.7744	Intermediate Similarity	NPC474487
0.7744	Intermediate Similarity	NPC131130
0.7744	Intermediate Similarity	NPC470671
0.7744	Intermediate Similarity	NPC470672
0.7744	Intermediate Similarity	NPC474504
0.774	Intermediate Similarity	NPC45449
0.774	Intermediate Similarity	NPC189689
0.774	Intermediate Similarity	NPC477834
0.7738	Intermediate Similarity	NPC299011
0.7738	Intermediate Similarity	NPC329678
0.7738	Intermediate Similarity	NPC5820
0.7738	Intermediate Similarity	NPC178343
0.7738	Intermediate Similarity	NPC124729
0.7738	Intermediate Similarity	NPC229190
0.7738	Intermediate Similarity	NPC306488
0.7735	Intermediate Similarity	NPC289244
0.7733	Intermediate Similarity	NPC311579
0.7733	Intermediate Similarity	NPC236756
0.7733	Intermediate Similarity	NPC192189
0.773	Intermediate Similarity	NPC470103
0.773	Intermediate Similarity	NPC121243
0.773	Intermediate Similarity	NPC240147
0.773	Intermediate Similarity	NPC187826
0.7727	Intermediate Similarity	NPC238995
0.7727	Intermediate Similarity	NPC475106
0.7727	Intermediate Similarity	NPC272722
0.7725	Intermediate Similarity	NPC158874
0.7722	Intermediate Similarity	NPC476159
0.7722	Intermediate Similarity	NPC169018
0.7719	Intermediate Similarity	NPC472423
0.7719	Intermediate Similarity	NPC295650
0.7719	Intermediate Similarity	NPC474744
0.7719	Intermediate Similarity	NPC474772
0.7719	Intermediate Similarity	NPC471675
0.7719	Intermediate Similarity	NPC76376
0.7719	Intermediate Similarity	NPC236769
0.7719	Intermediate Similarity	NPC472636
0.7716	Intermediate Similarity	NPC236974
0.7716	Intermediate Similarity	NPC144027
0.7714	Intermediate Similarity	NPC313368
0.7714	Intermediate Similarity	NPC172687
0.7714	Intermediate Similarity	NPC243701
0.7711	Intermediate Similarity	NPC90582
0.7711	Intermediate Similarity	NPC74397
0.7711	Intermediate Similarity	NPC171870
0.7711	Intermediate Similarity	NPC136840
0.7711	Intermediate Similarity	NPC310128
0.7711	Intermediate Similarity	NPC262094
0.7706	Intermediate Similarity	NPC159103
0.7706	Intermediate Similarity	NPC470461
0.7706	Intermediate Similarity	NPC477941
0.7702	Intermediate Similarity	NPC25937
0.7701	Intermediate Similarity	NPC210048
0.7697	Intermediate Similarity	NPC270913
0.7697	Intermediate Similarity	NPC143799
0.7697	Intermediate Similarity	NPC474061
0.7697	Intermediate Similarity	NPC475109
0.7697	Intermediate Similarity	NPC241838
0.7697	Intermediate Similarity	NPC323137
0.7697	Intermediate Similarity	NPC152042
0.7697	Intermediate Similarity	NPC230902
0.7692	Intermediate Similarity	NPC211466
0.7692	Intermediate Similarity	NPC3779
0.7692	Intermediate Similarity	NPC308200
0.7692	Intermediate Similarity	NPC17816
0.7692	Intermediate Similarity	NPC476182
0.7692	Intermediate Similarity	NPC176869
0.7692	Intermediate Similarity	NPC122828
0.7692	Intermediate Similarity	NPC91902
0.7692	Intermediate Similarity	NPC259632
0.7692	Intermediate Similarity	NPC44721
0.7692	Intermediate Similarity	NPC40086
0.7688	Intermediate Similarity	NPC255807
0.7688	Intermediate Similarity	NPC471456

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 NPC107283 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	386
0.1-0.2	1115
0.2-0.3	2158
0.3-0.4	2805
0.4-0.5	1665
0.5-0.6	748
0.6-0.7	224
0.7-0.8	48
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9625	High Similarity	NPD2403	Approved
0.7805	Intermediate Similarity	NPD2800	Approved
0.7746	Intermediate Similarity	NPD3882	Suspended
0.7679	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD1934	Approved
0.7429	Intermediate Similarity	NPD2801	Approved
0.7427	Intermediate Similarity	NPD1512	Approved
0.7412	Intermediate Similarity	NPD6799	Approved
0.7401	Intermediate Similarity	NPD7075	Discontinued
0.7386	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD1247	Approved
0.7365	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD6599	Discontinued
0.733	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD1549	Phase 2
0.7321	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD1240	Approved
0.731	Intermediate Similarity	NPD1511	Approved
0.7288	Intermediate Similarity	NPD3817	Phase 2
0.7273	Intermediate Similarity	NPD6801	Discontinued
0.7253	Intermediate Similarity	NPD6166	Phase 2
0.7253	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD1510	Phase 2
0.7229	Intermediate Similarity	NPD1607	Approved
0.7222	Intermediate Similarity	NPD5494	Approved
0.7207	Intermediate Similarity	NPD3749	Approved
0.7193	Intermediate Similarity	NPD2354	Approved
0.7174	Intermediate Similarity	NPD3818	Discontinued
0.7168	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD2532	Approved
0.7168	Intermediate Similarity	NPD2534	Approved
0.7168	Intermediate Similarity	NPD2533	Approved
0.7159	Intermediate Similarity	NPD4380	Phase 2
0.7143	Intermediate Similarity	NPD2370	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD6651	Approved
0.7119	Intermediate Similarity	NPD7411	Suspended
0.7119	Intermediate Similarity	NPD958	Approved
0.7113	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD4361	Phase 2
0.7111	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7104	Intermediate Similarity	NPD3926	Phase 2
0.7101	Intermediate Similarity	NPD2796	Approved
0.7086	Intermediate Similarity	NPD920	Approved
0.7072	Intermediate Similarity	NPD919	Approved
0.7062	Intermediate Similarity	NPD4363	Phase 3
0.7062	Intermediate Similarity	NPD4360	Phase 2
0.7059	Intermediate Similarity	NPD2344	Approved
0.7059	Intermediate Similarity	NPD2353	Approved
0.7059	Intermediate Similarity	NPD6797	Phase 2
0.7059	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD957	Approved
0.7035	Intermediate Similarity	NPD3750	Approved
0.7027	Intermediate Similarity	NPD7473	Discontinued
0.7021	Intermediate Similarity	NPD7251	Discontinued
0.6995	Remote Similarity	NPD6959	Discontinued
0.6994	Remote Similarity	NPD3887	Approved
0.6984	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD7808	Phase 3
0.6977	Remote Similarity	NPD1243	Approved
0.6973	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD6232	Discontinued
0.6944	Remote Similarity	NPD7819	Suspended
0.6915	Remote Similarity	NPD7074	Phase 3
0.6906	Remote Similarity	NPD5402	Approved
0.6897	Remote Similarity	NPD2309	Approved
0.6893	Remote Similarity	NPD5403	Approved
0.6875	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD5401	Approved
0.6862	Remote Similarity	NPD7054	Approved
0.6851	Remote Similarity	NPD1465	Phase 2
0.6839	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD8434	Phase 2
0.6825	Remote Similarity	NPD7472	Approved
0.6809	Remote Similarity	NPD3751	Discontinued
0.6807	Remote Similarity	NPD454	Approved
0.6806	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD1551	Phase 2
0.6802	Remote Similarity	NPD6099	Approved
0.6802	Remote Similarity	NPD6100	Approved
0.6789	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD6784	Approved
0.6788	Remote Similarity	NPD6785	Approved
0.6787	Remote Similarity	NPD1852	Discontinued
0.6782	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD7768	Phase 2
0.6765	Remote Similarity	NPD1184	Approved
0.6763	Remote Similarity	NPD1471	Phase 3
0.6761	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD6559	Discontinued
0.6744	Remote Similarity	NPD2799	Discontinued
0.6744	Remote Similarity	NPD3748	Approved
0.6744	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6743	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD5958	Discontinued
0.6722	Remote Similarity	NPD3226	Approved
0.6706	Remote Similarity	NPD943	Approved
0.6703	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD2654	Approved
0.6684	Remote Similarity	NPD7286	Phase 2
0.6684	Remote Similarity	NPD5711	Approved
0.6684	Remote Similarity	NPD5710	Approved
0.6667	Remote Similarity	NPD230	Phase 1
0.6667	Remote Similarity	NPD447	Suspended
0.6649	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD4628	Phase 3
0.6629	Remote Similarity	NPD4534	Discontinued
0.6627	Remote Similarity	NPD2598	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD5953	Discontinued
0.6609	Remote Similarity	NPD2935	Discontinued
0.6597	Remote Similarity	NPD5844	Phase 1
0.6596	Remote Similarity	NPD3787	Discontinued
0.6593	Remote Similarity	NPD4972	Discontinued
0.6588	Remote Similarity	NPD3268	Approved
0.657	Remote Similarity	NPD6355	Discontinued
0.6556	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6533	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD1163	Approved
0.6519	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6506	Remote Similarity	NPD9717	Approved
0.65	Remote Similarity	NPD1578	Phase 2
0.6491	Remote Similarity	NPD2313	Discontinued
0.6488	Remote Similarity	NPD1203	Approved
0.6471	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD4908	Phase 1
0.6467	Remote Similarity	NPD4749	Approved
0.6455	Remote Similarity	NPD7199	Phase 2
0.6452	Remote Similarity	NPD2296	Approved
0.6452	Remote Similarity	NPD2379	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.6447	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6446	Remote Similarity	NPD1610	Phase 2
0.6446	Remote Similarity	NPD422	Phase 1
0.6436	Remote Similarity	NPD6234	Discontinued
0.6432	Remote Similarity	NPD4287	Approved
0.6432	Remote Similarity	NPD37	Approved
0.6417	Remote Similarity	NPD4967	Phase 2
0.6417	Remote Similarity	NPD4965	Approved
0.6417	Remote Similarity	NPD4966	Approved
0.6412	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD3764	Approved
0.6392	Remote Similarity	NPD1729	Discontinued
0.6391	Remote Similarity	NPD987	Approved
0.6391	Remote Similarity	NPD3266	Approved
0.6391	Remote Similarity	NPD3267	Approved
0.6386	Remote Similarity	NPD6312	Discontinued
0.6384	Remote Similarity	NPD2346	Discontinued
0.6384	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6368	Remote Similarity	NPD3819	Phase 2
0.6364	Remote Similarity	NPD7033	Discontinued
0.6354	Remote Similarity	NPD7390	Discontinued
0.6354	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6353	Remote Similarity	NPD2798	Approved
0.6348	Remote Similarity	NPD2424	Discontinued
0.6335	Remote Similarity	NPD7229	Phase 3
0.6332	Remote Similarity	NPD8150	Discontinued
0.6322	Remote Similarity	NPD1613	Approved
0.6322	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.631	Remote Similarity	NPD5760	Phase 2
0.631	Remote Similarity	NPD1608	Approved
0.631	Remote Similarity	NPD5761	Phase 2
0.6301	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6301	Remote Similarity	NPD6798	Discontinued
0.6298	Remote Similarity	NPD5058	Phase 3
0.6294	Remote Similarity	NPD2797	Approved
0.6289	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD1933	Approved
0.6279	Remote Similarity	NPD6832	Phase 2
0.6277	Remote Similarity	NPD4288	Approved
0.6276	Remote Similarity	NPD7959	Clinical (unspecified phase)
0.6271	Remote Similarity	NPD4308	Phase 3
0.6271	Remote Similarity	NPD5588	Approved
0.625	Remote Similarity	NPD6808	Phase 2
0.625	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6244	Remote Similarity	NPD8014	Clinical (unspecified phase)
0.6244	Remote Similarity	NPD3658	Clinical (unspecified phase)
0.6244	Remote Similarity	NPD6104	Discontinued
0.6244	Remote Similarity	NPD6764	Approved
0.6244	Remote Similarity	NPD6765	Approved
0.6243	Remote Similarity	NPD6190	Approved
0.6236	Remote Similarity	NPD1501	Clinical (unspecified phase)
0.6232	Remote Similarity	NPD6781	Approved
0.6232	Remote Similarity	NPD6780	Approved
0.6232	Remote Similarity	NPD6776	Approved
0.6232	Remote Similarity	NPD6782	Approved
0.6232	Remote Similarity	NPD6778	Approved
0.6232	Remote Similarity	NPD6779	Approved
0.6232	Remote Similarity	NPD6777	Approved
0.623	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6229	Remote Similarity	NPD4060	Phase 1
0.6221	Remote Similarity	NPD9494	Approved

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