NPASS Compound

Structure

NPC87335 OpenBabel07101719252D 26 29 0 0 1 0 0 0 0 0999 V2000 -2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0981 2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 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 13 2 0 0 0 0 2 20 1 0 0 0 0 3 20 1 0 0 0 0 5 8 1 0 0 0 0 5 9 1 0 0 0 0 6 7 1 0 0 0 0 6 13 1 0 0 0 0 7 16 1 0 0 0 0 8 20 1 0 0 0 0 9 21 1 0 0 0 0 10 14 2 0 0 0 0 10 17 1 0 0 0 0 11 15 1 0 0 0 0 12 14 1 0 0 0 0 12 23 1 0 0 0 0 13 15 1 0 0 0 0 14 18 1 0 0 0 0 15 21 1 1 0 0 0 16 20 1 0 0 0 0 16 21 1 1 0 0 0 17 22 1 0 0 0 0 17 24 2 0 0 0 0 18 19 1 0 0 0 0 18 25 1 6 0 0 0 19 22 1 6 0 0 0 19 26 1 0 0 0 0 21 4 1 1 0 0 0 22 11 1 1 0 0 0 22 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	360.23
Volume:	382.094
LogP:	3.685
LogD:	2.127
LogS:	-3.035
# Rotatable Bonds:	3
TPSA:	66.9
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.618
Synthetic Accessibility Score:	4.936
Fsp3:	0.818
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.739
MDCK Permeability:	1.9688573956955224e-05
Pgp-inhibitor:	0.016
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.773
30% Bioavailability (F30%):	0.005

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.819
Plasma Protein Binding (PPB):	52.317039489746094%
Volume Distribution (VD):	1.358
Pgp-substrate:	59.099693298339844%

ADMET: Metabolism

CYP1A2-inhibitor:	0.012
CYP1A2-substrate:	0.471
CYP2C19-inhibitor:	0.027
CYP2C19-substrate:	0.8
CYP2C9-inhibitor:	0.078
CYP2C9-substrate:	0.087
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.567
CYP3A4-inhibitor:	0.13
CYP3A4-substrate:	0.326

ADMET: Excretion

Clearance (CL):	11.377
Half-life (T1/2):	0.676

ADMET: Toxicity

hERG Blockers:	0.022
Human Hepatotoxicity (H-HT):	0.168
Drug-inuced Liver Injury (DILI):	0.495
AMES Toxicity:	0.655
Rat Oral Acute Toxicity:	0.934
Maximum Recommended Daily Dose:	0.474
Skin Sensitization:	0.386
Carcinogencity:	0.881
Eye Corrosion:	0.094
Eye Irritation:	0.102
Respiratory Toxicity:	0.973

Download Data

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

Natural Product: NPC87335

Natural Product ID:	NPC87335
*Common Name:**	Macrophorin A
IUPAC Name:	(1R,2R,6R)-6-[[(1S,4aS,8aS)-5,5,8a-trimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]methyl]-2-hydroxy-3-(hydroxymethyl)-7-oxabicyclo[4.1.0]hept-3-en-5-one
Synonyms:
Standard InCHIKey:	OOIYDCZXWGFDDL-VKUFQHAMSA-N
Standard InCHI:	InChI=1S/C22H32O4/c1-13-6-7-16-20(2,3)8-5-9-21(16,4)15(13)11-22-17(24)10-14(12-23)18(25)19(22)26-22/h10,15-16,18-19,23,25H,1,5-9,11-12H2,2-4H3/t15-,16-,18+,19+,21+,22-/m0/s1
SMILES:	C=C1CC[C@H]2C(C)(C)CCC[C@]2(C)[C@H]1C[C@]12C(=O)C=C(CO)[C@H]([C@H]1O2)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3609688
PubChem CID:	158854
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0001831] Carbonyl compounds [CHEMONTID:0000118] Ketones [CHEMONTID:0003487] Cyclic ketones [CHEMONTID:0004325] Cyclohexenones

*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
NPO33112	guignardia mangiferae	Species	Phyllostictaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26241103]

☑ 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	1

Activity Type	# Activity
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	4500.0	nM	PMID[560310]

☑ 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 NPC87335 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	232
0.1-0.2	1327
0.2-0.3	4252
0.3-0.4	8005
0.4-0.5	13448
0.5-0.6	7682
0.6-0.7	6092
0.7-0.8	1597
0.8-0.85	47
0.85-0.9	8
0.9-0.95	2
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9118	High Similarity	NPC131366
0.9057	High Similarity	NPC317107
0.902	High Similarity	NPC478176
0.8972	High Similarity	NPC317687
0.8922	High Similarity	NPC207885
0.8922	High Similarity	NPC112613
0.8812	High Similarity	NPC471916
0.8774	High Similarity	NPC322903
0.8679	High Similarity	NPC473165
0.8654	High Similarity	NPC39996
0.8585	High Similarity	NPC166607
0.8571	High Similarity	NPC251310
0.8545	High Similarity	NPC477266
0.8545	High Similarity	NPC317210
0.8534	High Similarity	NPC225049
0.8529	High Similarity	NPC94337
0.8509	High Similarity	NPC67569
0.8491	Intermediate Similarity	NPC160843
0.8491	Intermediate Similarity	NPC72255
0.8468	Intermediate Similarity	NPC80650
0.8435	Intermediate Similarity	NPC470265
0.8435	Intermediate Similarity	NPC23786
0.8421	Intermediate Similarity	NPC478051
0.8407	Intermediate Similarity	NPC709
0.8407	Intermediate Similarity	NPC50774
0.84	Intermediate Similarity	NPC477684
0.8396	Intermediate Similarity	NPC247957
0.8396	Intermediate Similarity	NPC249187
0.8381	Intermediate Similarity	NPC476897
0.8378	Intermediate Similarity	NPC159333
0.8364	Intermediate Similarity	NPC476023
0.8362	Intermediate Similarity	NPC469789
0.8362	Intermediate Similarity	NPC67251
0.8333	Intermediate Similarity	NPC196227
0.8333	Intermediate Similarity	NPC67321
0.8333	Intermediate Similarity	NPC187435
0.8319	Intermediate Similarity	NPC470492
0.8319	Intermediate Similarity	NPC140055
0.8319	Intermediate Similarity	NPC27999
0.8319	Intermediate Similarity	NPC470493
0.8319	Intermediate Similarity	NPC477116
0.8319	Intermediate Similarity	NPC167606
0.8319	Intermediate Similarity	NPC286528
0.8319	Intermediate Similarity	NPC20302
0.8319	Intermediate Similarity	NPC312824
0.8319	Intermediate Similarity	NPC183580
0.8317	Intermediate Similarity	NPC116726
0.8317	Intermediate Similarity	NPC73457
0.8305	Intermediate Similarity	NPC473253
0.8291	Intermediate Similarity	NPC470922
0.8291	Intermediate Similarity	NPC476729
0.8291	Intermediate Similarity	NPC8374
0.8288	Intermediate Similarity	NPC269530
0.8288	Intermediate Similarity	NPC207251
0.8273	Intermediate Similarity	NPC76084
0.8261	Intermediate Similarity	NPC474370
0.8257	Intermediate Similarity	NPC151393
0.8246	Intermediate Similarity	NPC17772
0.8246	Intermediate Similarity	NPC186525
0.8246	Intermediate Similarity	NPC470776
0.8246	Intermediate Similarity	NPC297179
0.8241	Intermediate Similarity	NPC257353
0.823	Intermediate Similarity	NPC40632
0.823	Intermediate Similarity	NPC179626
0.823	Intermediate Similarity	NPC328374
0.823	Intermediate Similarity	NPC474734
0.823	Intermediate Similarity	NPC96312
0.823	Intermediate Similarity	NPC270929
0.823	Intermediate Similarity	NPC207217
0.823	Intermediate Similarity	NPC251236
0.8224	Intermediate Similarity	NPC469980
0.8224	Intermediate Similarity	NPC104161
0.8224	Intermediate Similarity	NPC95899
0.8224	Intermediate Similarity	NPC118902
0.8224	Intermediate Similarity	NPC478057
0.822	Intermediate Similarity	NPC293112
0.8214	Intermediate Similarity	NPC73300
0.8214	Intermediate Similarity	NPC208998
0.8214	Intermediate Similarity	NPC198539
0.8214	Intermediate Similarity	NPC477126
0.8214	Intermediate Similarity	NPC7921
0.8214	Intermediate Similarity	NPC108721
0.8208	Intermediate Similarity	NPC97435
0.8205	Intermediate Similarity	NPC120724
0.8205	Intermediate Similarity	NPC265557
0.8205	Intermediate Similarity	NPC105926
0.8205	Intermediate Similarity	NPC91693
0.8205	Intermediate Similarity	NPC18945
0.8198	Intermediate Similarity	NPC207689
0.8198	Intermediate Similarity	NPC146945
0.8198	Intermediate Similarity	NPC171888
0.8198	Intermediate Similarity	NPC474229
0.819	Intermediate Similarity	NPC477046
0.819	Intermediate Similarity	NPC102822
0.8182	Intermediate Similarity	NPC141350
0.8182	Intermediate Similarity	NPC476193
0.8174	Intermediate Similarity	NPC473274
0.8174	Intermediate Similarity	NPC61520
0.8174	Intermediate Similarity	NPC268958
0.8174	Intermediate Similarity	NPC264954
0.8173	Intermediate Similarity	NPC91439
0.8167	Intermediate Similarity	NPC470880
0.8165	Intermediate Similarity	NPC3316
0.8165	Intermediate Similarity	NPC220229
0.8165	Intermediate Similarity	NPC144854
0.8165	Intermediate Similarity	NPC475060
0.8165	Intermediate Similarity	NPC83744
0.8158	Intermediate Similarity	NPC97908
0.8158	Intermediate Similarity	NPC470775
0.8158	Intermediate Similarity	NPC287343
0.8158	Intermediate Similarity	NPC176513
0.8158	Intermediate Similarity	NPC122033
0.8158	Intermediate Similarity	NPC474654
0.8158	Intermediate Similarity	NPC469684
0.8158	Intermediate Similarity	NPC470854
0.8158	Intermediate Similarity	NPC243065
0.8155	Intermediate Similarity	NPC472976
0.8155	Intermediate Similarity	NPC472977
0.8142	Intermediate Similarity	NPC247069
0.8142	Intermediate Similarity	NPC326542
0.8142	Intermediate Similarity	NPC473798
0.8142	Intermediate Similarity	NPC117712
0.8137	Intermediate Similarity	NPC475441
0.8136	Intermediate Similarity	NPC8369
0.8136	Intermediate Similarity	NPC81736
0.8136	Intermediate Similarity	NPC24651
0.8136	Intermediate Similarity	NPC172154
0.8125	Intermediate Similarity	NPC473877
0.8125	Intermediate Similarity	NPC472002
0.812	Intermediate Similarity	NPC88326
0.812	Intermediate Similarity	NPC153700
0.812	Intermediate Similarity	NPC312833
0.8113	Intermediate Similarity	NPC154072
0.8108	Intermediate Similarity	NPC161816
0.8108	Intermediate Similarity	NPC115257
0.8103	Intermediate Similarity	NPC112038
0.8095	Intermediate Similarity	NPC272451
0.8091	Intermediate Similarity	NPC192813
0.8091	Intermediate Similarity	NPC293850
0.8091	Intermediate Similarity	NPC277017
0.8091	Intermediate Similarity	NPC217201
0.8091	Intermediate Similarity	NPC469916
0.8091	Intermediate Similarity	NPC472439
0.8091	Intermediate Similarity	NPC329417
0.8091	Intermediate Similarity	NPC306265
0.8091	Intermediate Similarity	NPC154608
0.8087	Intermediate Similarity	NPC329736
0.8087	Intermediate Similarity	NPC240509
0.8083	Intermediate Similarity	NPC477713
0.8083	Intermediate Similarity	NPC477712
0.8083	Intermediate Similarity	NPC476859
0.8077	Intermediate Similarity	NPC272617
0.8077	Intermediate Similarity	NPC476245
0.8077	Intermediate Similarity	NPC53565
0.8077	Intermediate Similarity	NPC271195
0.8073	Intermediate Similarity	NPC470587
0.8073	Intermediate Similarity	NPC260268
0.8073	Intermediate Similarity	NPC48733
0.8073	Intermediate Similarity	NPC150531
0.8073	Intermediate Similarity	NPC149047
0.8073	Intermediate Similarity	NPC50692
0.8073	Intermediate Similarity	NPC296945
0.8073	Intermediate Similarity	NPC476027
0.8073	Intermediate Similarity	NPC214264
0.8073	Intermediate Similarity	NPC171137
0.8073	Intermediate Similarity	NPC152695
0.8073	Intermediate Similarity	NPC202167
0.8073	Intermediate Similarity	NPC85829
0.8073	Intermediate Similarity	NPC49958
0.8073	Intermediate Similarity	NPC302607
0.8073	Intermediate Similarity	NPC319077
0.8073	Intermediate Similarity	NPC97202
0.807	Intermediate Similarity	NPC134869
0.807	Intermediate Similarity	NPC270478
0.807	Intermediate Similarity	NPC474046
0.807	Intermediate Similarity	NPC235539
0.807	Intermediate Similarity	NPC152199
0.807	Intermediate Similarity	NPC470628
0.807	Intermediate Similarity	NPC259306
0.8056	Intermediate Similarity	NPC159533
0.8056	Intermediate Similarity	NPC99266
0.8053	Intermediate Similarity	NPC51978
0.8053	Intermediate Similarity	NPC49451
0.8053	Intermediate Similarity	NPC122056
0.8053	Intermediate Similarity	NPC250109
0.8051	Intermediate Similarity	NPC11895
0.8039	Intermediate Similarity	NPC473099
0.8037	Intermediate Similarity	NPC470184
0.8034	Intermediate Similarity	NPC470878
0.8034	Intermediate Similarity	NPC470779
0.8034	Intermediate Similarity	NPC473256
0.8019	Intermediate Similarity	NPC264378
0.8019	Intermediate Similarity	NPC478056
0.8018	Intermediate Similarity	NPC11710
0.8018	Intermediate Similarity	NPC20192
0.8018	Intermediate Similarity	NPC475922
0.8018	Intermediate Similarity	NPC214644
0.8017	Intermediate Similarity	NPC476851
0.8017	Intermediate Similarity	NPC473593
0.8017	Intermediate Similarity	NPC472933

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 NPC87335 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	201
0.1-0.2	1631
0.2-0.3	3691
0.3-0.4	2374
0.4-0.5	770
0.5-0.6	241
0.6-0.7	205
0.7-0.8	37
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
0.8319	Intermediate Similarity	NPD7115	Discovery
0.7797	Intermediate Similarity	NPD6054	Approved
0.7797	Intermediate Similarity	NPD6319	Approved
0.7797	Intermediate Similarity	NPD6059	Approved
0.7788	Intermediate Similarity	NPD4634	Approved
0.775	Intermediate Similarity	NPD8328	Phase 3
0.7748	Intermediate Similarity	NPD6402	Approved
0.7748	Intermediate Similarity	NPD7128	Approved
0.7748	Intermediate Similarity	NPD5739	Approved
0.7748	Intermediate Similarity	NPD6675	Approved
0.7699	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7699	Intermediate Similarity	NPD6372	Approved
0.7699	Intermediate Similarity	NPD6373	Approved
0.7685	Intermediate Similarity	NPD4225	Approved
0.7667	Intermediate Similarity	NPD6370	Approved
0.7652	Intermediate Similarity	NPD8297	Approved
0.7636	Intermediate Similarity	NPD5211	Phase 2
0.7611	Intermediate Similarity	NPD6881	Approved
0.7611	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7611	Intermediate Similarity	NPD6899	Approved
0.7611	Intermediate Similarity	NPD7320	Approved
0.7593	Intermediate Similarity	NPD4755	Approved
0.7583	Intermediate Similarity	NPD6015	Approved
0.7583	Intermediate Similarity	NPD6016	Approved
0.7565	Intermediate Similarity	NPD6649	Approved
0.7565	Intermediate Similarity	NPD6650	Approved
0.7541	Intermediate Similarity	NPD7492	Approved
0.7522	Intermediate Similarity	NPD5701	Approved
0.7522	Intermediate Similarity	NPD5697	Approved
0.7521	Intermediate Similarity	NPD5988	Approved
0.75	Intermediate Similarity	NPD5141	Approved
0.748	Intermediate Similarity	NPD6616	Approved
0.7478	Intermediate Similarity	NPD6883	Approved
0.7478	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7478	Intermediate Similarity	NPD7290	Approved
0.7478	Intermediate Similarity	NPD7102	Approved
0.7476	Intermediate Similarity	NPD3618	Phase 1
0.7455	Intermediate Similarity	NPD5285	Approved
0.7455	Intermediate Similarity	NPD5286	Approved
0.7455	Intermediate Similarity	NPD4700	Approved
0.7455	Intermediate Similarity	NPD4696	Approved
0.7436	Intermediate Similarity	NPD4632	Approved
0.7431	Intermediate Similarity	NPD7902	Approved
0.7431	Intermediate Similarity	NPD6084	Phase 2
0.7431	Intermediate Similarity	NPD6083	Phase 2
0.7419	Intermediate Similarity	NPD7078	Approved
0.7419	Intermediate Similarity	NPD8293	Discontinued
0.7414	Intermediate Similarity	NPD8130	Phase 1
0.7414	Intermediate Similarity	NPD6617	Approved
0.7414	Intermediate Similarity	NPD6869	Approved
0.7414	Intermediate Similarity	NPD6847	Approved
0.7395	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD6012	Approved
0.7391	Intermediate Similarity	NPD6014	Approved
0.7391	Intermediate Similarity	NPD6013	Approved
0.7368	Intermediate Similarity	NPD6412	Phase 2
0.736	Intermediate Similarity	NPD7736	Approved
0.735	Intermediate Similarity	NPD6882	Approved
0.7339	Intermediate Similarity	NPD4697	Phase 3
0.7321	Intermediate Similarity	NPD5224	Approved
0.7321	Intermediate Similarity	NPD5225	Approved
0.7321	Intermediate Similarity	NPD4633	Approved
0.7321	Intermediate Similarity	NPD5226	Approved
0.7317	Intermediate Similarity	NPD7604	Phase 2
0.7315	Intermediate Similarity	NPD7748	Approved
0.7304	Intermediate Similarity	NPD6011	Approved
0.7297	Intermediate Similarity	NPD7640	Approved
0.7297	Intermediate Similarity	NPD7639	Approved
0.729	Intermediate Similarity	NPD7515	Phase 2
0.7281	Intermediate Similarity	NPD6008	Approved
0.7265	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7264	Intermediate Similarity	NPD5328	Approved
0.7264	Intermediate Similarity	NPD4753	Phase 2
0.7257	Intermediate Similarity	NPD5175	Approved
0.7257	Intermediate Similarity	NPD5174	Approved
0.725	Intermediate Similarity	NPD6009	Approved
0.7232	Intermediate Similarity	NPD5223	Approved
0.7222	Intermediate Similarity	NPD6399	Phase 3
0.7222	Intermediate Similarity	NPD4202	Approved
0.7222	Intermediate Similarity	NPD6033	Approved
0.7217	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD5696	Approved
0.7207	Intermediate Similarity	NPD7638	Approved
0.7182	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD5221	Approved
0.7182	Intermediate Similarity	NPD5222	Approved
0.7179	Intermediate Similarity	NPD6371	Approved
0.7156	Intermediate Similarity	NPD5282	Discontinued
0.7156	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD7900	Approved
0.7155	Intermediate Similarity	NPD6686	Approved
0.7154	Intermediate Similarity	NPD5983	Phase 2
0.7143	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD4767	Approved
0.713	Intermediate Similarity	NPD4768	Approved
0.713	Intermediate Similarity	NPD6079	Approved
0.7117	Intermediate Similarity	NPD5173	Approved
0.7115	Intermediate Similarity	NPD4786	Approved
0.7105	Intermediate Similarity	NPD4754	Approved
0.7094	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD5695	Phase 3
0.7091	Intermediate Similarity	NPD4629	Approved
0.7091	Intermediate Similarity	NPD5210	Approved
0.7087	Intermediate Similarity	NPD3667	Approved
0.708	Intermediate Similarity	NPD5344	Discontinued
0.7064	Intermediate Similarity	NPD5779	Approved
0.7064	Intermediate Similarity	NPD5778	Approved
0.7063	Intermediate Similarity	NPD6336	Discontinued
0.7059	Intermediate Similarity	NPD4695	Discontinued
0.7037	Intermediate Similarity	NPD46	Approved
0.7037	Intermediate Similarity	NPD6698	Approved
0.7031	Intermediate Similarity	NPD7319	Approved
0.7025	Intermediate Similarity	NPD6274	Approved
0.7009	Intermediate Similarity	NPD6672	Approved
0.7009	Intermediate Similarity	NPD4730	Approved
0.7009	Intermediate Similarity	NPD4729	Approved
0.7009	Intermediate Similarity	NPD5128	Approved
0.7009	Intermediate Similarity	NPD5737	Approved
0.6992	Remote Similarity	NPD7100	Approved
0.6992	Remote Similarity	NPD7101	Approved
0.6952	Remote Similarity	NPD3665	Phase 1
0.6952	Remote Similarity	NPD3666	Approved
0.6952	Remote Similarity	NPD3133	Approved
0.6929	Remote Similarity	NPD7507	Approved
0.6911	Remote Similarity	NPD6335	Approved
0.6891	Remote Similarity	NPD5248	Approved
0.6891	Remote Similarity	NPD5251	Approved
0.6891	Remote Similarity	NPD5249	Phase 3
0.6891	Remote Similarity	NPD5250	Approved
0.6891	Remote Similarity	NPD5247	Approved
0.6887	Remote Similarity	NPD5329	Approved
0.688	Remote Similarity	NPD6908	Approved
0.688	Remote Similarity	NPD6909	Approved
0.688	Remote Similarity	NPD6921	Approved
0.6857	Remote Similarity	NPD6110	Phase 1
0.6855	Remote Similarity	NPD4522	Approved
0.6833	Remote Similarity	NPD5217	Approved
0.6833	Remote Similarity	NPD5216	Approved
0.6833	Remote Similarity	NPD5215	Approved
0.6829	Remote Similarity	NPD6317	Approved
0.6822	Remote Similarity	NPD4519	Discontinued
0.6822	Remote Similarity	NPD4623	Approved
0.6822	Remote Similarity	NPD5279	Phase 3
0.6818	Remote Similarity	NPD6411	Approved
0.6792	Remote Similarity	NPD4197	Approved
0.6789	Remote Similarity	NPD6673	Approved
0.6789	Remote Similarity	NPD6080	Approved
0.6789	Remote Similarity	NPD6904	Approved
0.6786	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.678	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD6313	Approved
0.6774	Remote Similarity	NPD6314	Approved
0.6759	Remote Similarity	NPD7524	Approved
0.675	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.675	Remote Similarity	NPD5135	Approved
0.675	Remote Similarity	NPD5169	Approved
0.6748	Remote Similarity	NPD6868	Approved
0.6746	Remote Similarity	NPD8513	Phase 3
0.6746	Remote Similarity	NPD8517	Approved
0.6746	Remote Similarity	NPD8516	Approved
0.6746	Remote Similarity	NPD8515	Approved
0.6729	Remote Similarity	NPD1696	Phase 3
0.6724	Remote Similarity	NPD7632	Discontinued
0.6718	Remote Similarity	NPD5956	Approved
0.6696	Remote Similarity	NPD6648	Approved
0.6694	Remote Similarity	NPD5127	Approved
0.6667	Remote Similarity	NPD7521	Approved
0.6667	Remote Similarity	NPD7146	Approved
0.6667	Remote Similarity	NPD5330	Approved
0.6667	Remote Similarity	NPD7983	Approved
0.6667	Remote Similarity	NPD7334	Approved
0.6667	Remote Similarity	NPD6684	Approved
0.6667	Remote Similarity	NPD5693	Phase 1
0.6667	Remote Similarity	NPD6409	Approved
0.6667	Remote Similarity	NPD7637	Suspended
0.6641	Remote Similarity	NPD6067	Discontinued
0.664	Remote Similarity	NPD7327	Approved
0.664	Remote Similarity	NPD7328	Approved
0.6636	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD6101	Approved
0.6636	Remote Similarity	NPD3668	Phase 3
0.6636	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD7645	Phase 2
0.6614	Remote Similarity	NPD8033	Approved
0.6614	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD3573	Approved
0.6604	Remote Similarity	NPD4223	Phase 3
0.6604	Remote Similarity	NPD4221	Approved
0.6587	Remote Similarity	NPD7516	Approved
0.6583	Remote Similarity	NPD5168	Approved
0.6571	Remote Similarity	NPD7525	Registered
0.6571	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD6903	Approved
0.6542	Remote Similarity	NPD6695	Phase 3
0.6538	Remote Similarity	NPD3617	Approved
0.6535	Remote Similarity	NPD8294	Approved
0.6535	Remote Similarity	NPD8377	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