NPASS Compound

Structure

CID1704 OpenBabel06191715322D 21 22 0 0 1 0 0 0 0 0999 V2000 0.8659 -1.5004 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5982 -0.4994 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5990 2.4992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5987 1.4991 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7332 2.9993 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7326 0.9992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8670 2.4997 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7323 -0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0009 2.9998 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7312 3.0004 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5977 1.5006 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8662 -0.5004 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8653 2.5002 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5974 2.5007 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7318 1.0004 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8656 1.5001 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0003 0.9997 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4633 3.0009 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8665 1.4994 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7320 0.0004 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 2 20 1 0 0 0 0 3 4 1 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 7 1 0 0 0 0 6 8 1 0 0 0 0 7 9 1 0 0 0 0 8 12 1 0 0 0 0 9 13 1 0 0 0 0 10 13 2 0 0 0 0 10 14 1 0 0 0 0 11 14 2 0 0 0 0 11 15 1 0 0 0 0 12 1 1 1 0 0 0 12 21 1 0 0 0 0 13 16 1 0 0 0 0 14 18 1 0 0 0 0 15 16 2 0 0 0 0 15 20 1 0 0 0 0 16 17 1 0 0 0 0 17 19 2 0 0 0 0 17 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	292.17
Volume:	310.09
LogP:	4.542
LogD:	3.78
LogS:	-4.554
# Rotatable Bonds:	1
TPSA:	55.76
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.799
Synthetic Accessibility Score:	3.168
Fsp3:	0.588
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.698
MDCK Permeability:	3.428685522521846e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.926
30% Bioavailability (F30%):	0.149

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.777
Plasma Protein Binding (PPB):	96.52444458007812%
Volume Distribution (VD):	1.12
Pgp-substrate:	2.0981359481811523%

ADMET: Metabolism

CYP1A2-inhibitor:	0.965
CYP1A2-substrate:	0.668
CYP2C19-inhibitor:	0.907
CYP2C19-substrate:	0.21
CYP2C9-inhibitor:	0.718
CYP2C9-substrate:	0.964
CYP2D6-inhibitor:	0.868
CYP2D6-substrate:	0.838
CYP3A4-inhibitor:	0.664
CYP3A4-substrate:	0.094

ADMET: Excretion

Clearance (CL):	9.005
Half-life (T1/2):	0.437

ADMET: Toxicity

hERG Blockers:	0.03
Human Hepatotoxicity (H-HT):	0.078
Drug-inuced Liver Injury (DILI):	0.482
AMES Toxicity:	0.037
Rat Oral Acute Toxicity:	0.02
Maximum Recommended Daily Dose:	0.698
Skin Sensitization:	0.918
Carcinogencity:	0.072
Eye Corrosion:	0.067
Eye Irritation:	0.937
Respiratory Toxicity:	0.634

Download Data

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

Natural Product: NPC1704

Natural Product ID:	NPC1704
*Common Name:**	(R)-Lasiodiplodin
IUPAC Name:	(9R)-15-hydroxy-13-methoxy-9-methyl-10-oxabicyclo[10.4.0]hexadeca-1(16),12,14-trien-11-one
Synonyms:	(R)-Lasiodiplodin
Standard InCHIKey:	OKWRDLQBKAOJNC-GFCCVEGCSA-N
Standard InCHI:	InChI=1S/C17H24O4/c1-12-8-6-4-3-5-7-9-13-10-14(18)11-15(20-2)16(13)17(19)21-12/h10-12,18H,3-9H2,1-2H3/t12-/m1/s1
SMILES:	C[C@@H]1CCCCCCCc2cc(cc(c2C(=O)O1)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1669748
PubChem CID:	11833217
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000147] Macrolides and analogues

*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
NPO32516	ficus auriculata	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25008455]
NPO16865.1	Prunus serrulata var. spontanea	Varieties	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO16865.1	Prunus serrulata var. spontanea	Varieties	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16885	Phonus arborescens	Species	Asteraceae	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	3

Activity Type	# Activity
NON-MOLECULAR	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	3.45	%	PMID[502115]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	14.19	%	PMID[502115]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	51.55	%	PMID[502115]

☑ 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 NPC1704 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	322
0.1-0.2	1444
0.2-0.3	3622
0.3-0.4	7954
0.4-0.5	10568
0.5-0.6	3477
0.6-0.7	5684
0.7-0.8	6909
0.8-0.85	2010
0.85-0.9	545
0.9-0.95	135
0.95-1	27

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC67650
0.9853	High Similarity	NPC51106
0.9853	High Similarity	NPC472006
0.9779	High Similarity	NPC474385
0.9708	High Similarity	NPC469542
0.9706	High Similarity	NPC475730
0.9701	High Similarity	NPC70380
0.9701	High Similarity	NPC135837
0.964	High Similarity	NPC107625
0.9638	High Similarity	NPC277426
0.9638	High Similarity	NPC280404
0.9638	High Similarity	NPC86373
0.9638	High Similarity	NPC210425
0.9635	High Similarity	NPC469579
0.963	High Similarity	NPC191835
0.963	High Similarity	NPC212693
0.963	High Similarity	NPC94248
0.9568	High Similarity	NPC472034
0.9552	High Similarity	NPC182496
0.9552	High Similarity	NPC180905
0.95	High Similarity	NPC472033
0.9493	High Similarity	NPC250755
0.9485	High Similarity	NPC478200
0.9485	High Similarity	NPC33144
0.9485	High Similarity	NPC472602
0.9433	High Similarity	NPC210320
0.9433	High Similarity	NPC472036
0.9429	High Similarity	NPC134621
0.942	High Similarity	NPC158634
0.942	High Similarity	NPC313123
0.942	High Similarity	NPC53649
0.942	High Similarity	NPC90411
0.942	High Similarity	NPC478217
0.9416	High Similarity	NPC32360
0.9416	High Similarity	NPC139634
0.9416	High Similarity	NPC105456
0.9412	High Similarity	NPC71256
0.9403	High Similarity	NPC153783
0.9371	High Similarity	NPC469670
0.9371	High Similarity	NPC469619
0.9366	High Similarity	NPC471641
0.9366	High Similarity	NPC240253
0.9366	High Similarity	NPC471642
0.9366	High Similarity	NPC73411
0.9366	High Similarity	NPC215711
0.9366	High Similarity	NPC240622
0.9362	High Similarity	NPC237208
0.9357	High Similarity	NPC66404
0.9357	High Similarity	NPC95123
0.9348	High Similarity	NPC472601
0.9348	High Similarity	NPC165172
0.9348	High Similarity	NPC158472
0.9348	High Similarity	NPC472600
0.9338	High Similarity	NPC235115
0.9306	High Similarity	NPC240768
0.9306	High Similarity	NPC70016
0.9306	High Similarity	NPC215921
0.9306	High Similarity	NPC200773
0.9301	High Similarity	NPC270160
0.9301	High Similarity	NPC237440
0.9301	High Similarity	NPC476684
0.9291	High Similarity	NPC29577
0.9291	High Similarity	NPC312789
0.9286	High Similarity	NPC159721
0.9286	High Similarity	NPC478202
0.9281	High Similarity	NPC478201
0.9281	High Similarity	NPC472605
0.9281	High Similarity	NPC472603
0.9281	High Similarity	NPC472604
0.9281	High Similarity	NPC472035
0.9275	High Similarity	NPC268052
0.927	High Similarity	NPC178467
0.927	High Similarity	NPC474849
0.927	High Similarity	NPC194579
0.927	High Similarity	NPC149372
0.927	High Similarity	NPC65837
0.927	High Similarity	NPC474771
0.9254	High Similarity	NPC219892
0.9254	High Similarity	NPC189823
0.9225	High Similarity	NPC163846
0.9225	High Similarity	NPC225173
0.922	High Similarity	NPC151607
0.922	High Similarity	NPC42540
0.9214	High Similarity	NPC105648
0.9214	High Similarity	NPC96692
0.9203	High Similarity	NPC475974
0.9191	High Similarity	NPC175943
0.9167	High Similarity	NPC4423
0.9167	High Similarity	NPC291049
0.9167	High Similarity	NPC233267
0.9167	High Similarity	NPC77325
0.9161	High Similarity	NPC8817
0.9161	High Similarity	NPC125801
0.9161	High Similarity	NPC14098
0.9155	High Similarity	NPC83272
0.9155	High Similarity	NPC473692
0.9155	High Similarity	NPC75694
0.9149	High Similarity	NPC471643
0.9149	High Similarity	NPC472610
0.9149	High Similarity	NPC471731
0.9149	High Similarity	NPC471639
0.9143	High Similarity	NPC220106
0.9143	High Similarity	NPC244923
0.9137	High Similarity	NPC88269
0.9116	High Similarity	NPC79998
0.9116	High Similarity	NPC99381
0.9116	High Similarity	NPC16082
0.9116	High Similarity	NPC82592
0.911	High Similarity	NPC273483
0.911	High Similarity	NPC167903
0.9103	High Similarity	NPC179178
0.9103	High Similarity	NPC475460
0.9103	High Similarity	NPC60413
0.9097	High Similarity	NPC37139
0.9097	High Similarity	NPC153417
0.9097	High Similarity	NPC172329
0.9097	High Similarity	NPC105415
0.9097	High Similarity	NPC2569
0.9091	High Similarity	NPC473023
0.9091	High Similarity	NPC470357
0.9091	High Similarity	NPC267509
0.9085	High Similarity	NPC210966
0.9085	High Similarity	NPC126882
0.9085	High Similarity	NPC478203
0.9085	High Similarity	NPC470932
0.9078	High Similarity	NPC471640
0.9078	High Similarity	NPC49108
0.9078	High Similarity	NPC471733
0.9078	High Similarity	NPC471644
0.9071	High Similarity	NPC155205
0.9065	High Similarity	NPC9121
0.9065	High Similarity	NPC177307
0.9065	High Similarity	NPC472403
0.9058	High Similarity	NPC50455
0.9058	High Similarity	NPC158481
0.9054	High Similarity	NPC150227
0.9054	High Similarity	NPC472050
0.9048	High Similarity	NPC472799
0.9048	High Similarity	NPC281477
0.9044	High Similarity	NPC476389
0.9041	High Similarity	NPC133856
0.9034	High Similarity	NPC6923
0.903	High Similarity	NPC293453
0.9028	High Similarity	NPC137296
0.9028	High Similarity	NPC12305
0.9021	High Similarity	NPC257558
0.9021	High Similarity	NPC32470
0.9014	High Similarity	NPC310340
0.9007	High Similarity	NPC16455
0.9007	High Similarity	NPC37530
0.9007	High Similarity	NPC307990
0.9	High Similarity	NPC52358
0.9	High Similarity	NPC275356
0.9	High Similarity	NPC247409
0.9	High Similarity	NPC474655
0.9	High Similarity	NPC92655
0.8993	High Similarity	NPC190020
0.8993	High Similarity	NPC470398
0.8993	High Similarity	NPC84935
0.8993	High Similarity	NPC470397
0.8993	High Similarity	NPC77679
0.8986	High Similarity	NPC89625
0.8986	High Similarity	NPC142027
0.8986	High Similarity	NPC27407
0.8986	High Similarity	NPC144027
0.8986	High Similarity	NPC149618
0.8986	High Similarity	NPC236974
0.8986	High Similarity	NPC199926
0.8978	High Similarity	NPC203817
0.8973	High Similarity	NPC96501
0.8973	High Similarity	NPC150928
0.8973	High Similarity	NPC158866
0.8973	High Similarity	NPC309979
0.8973	High Similarity	NPC307780
0.8973	High Similarity	NPC119929
0.8966	High Similarity	NPC221352
0.8958	High Similarity	NPC138978
0.8958	High Similarity	NPC260946
0.8951	High Similarity	NPC184702
0.8944	High Similarity	NPC297985
0.8944	High Similarity	NPC82913
0.8936	High Similarity	NPC99441
0.8933	High Similarity	NPC470339
0.8926	High Similarity	NPC227062
0.8921	High Similarity	NPC242712
0.8921	High Similarity	NPC84699
0.8921	High Similarity	NPC291454
0.8912	High Similarity	NPC72958
0.8912	High Similarity	NPC232645
0.8912	High Similarity	NPC204350
0.8905	High Similarity	NPC470160
0.8897	High Similarity	NPC471734
0.8897	High Similarity	NPC17840
0.8897	High Similarity	NPC247477
0.8897	High Similarity	NPC42292
0.8897	High Similarity	NPC307732
0.8881	High Similarity	NPC354984
0.8881	High Similarity	NPC84266
0.8881	High Similarity	NPC73028
0.8874	High Similarity	NPC472055

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 NPC1704 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	273
0.1-0.2	964
0.2-0.3	1755
0.3-0.4	2509
0.4-0.5	1848
0.5-0.6	1146
0.6-0.7	456
0.7-0.8	160
0.8-0.85	34
0.85-0.9	2
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9416	High Similarity	NPD970	Clinical (unspecified phase)
0.9155	High Similarity	NPD2533	Approved
0.9155	High Similarity	NPD2534	Approved
0.9155	High Similarity	NPD2532	Approved
0.8792	High Similarity	NPD7819	Suspended
0.8531	High Similarity	NPD1550	Clinical (unspecified phase)
0.8531	High Similarity	NPD1552	Clinical (unspecified phase)
0.8521	High Similarity	NPD1510	Phase 2
0.85	High Similarity	NPD1240	Approved
0.8472	Intermediate Similarity	NPD1549	Phase 2
0.8421	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8397	Intermediate Similarity	NPD6232	Discontinued
0.838	Intermediate Similarity	NPD1607	Approved
0.8378	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8377	Intermediate Similarity	NPD7075	Discontinued
0.8356	Intermediate Similarity	NPD3750	Approved
0.8355	Intermediate Similarity	NPD1934	Approved
0.8333	Intermediate Similarity	NPD2796	Approved
0.8333	Intermediate Similarity	NPD2935	Discontinued
0.8333	Intermediate Similarity	NPD6959	Discontinued
0.8311	Intermediate Similarity	NPD6799	Approved
0.8301	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8289	Intermediate Similarity	NPD7411	Suspended
0.828	Intermediate Similarity	NPD5710	Approved
0.828	Intermediate Similarity	NPD5711	Approved
0.8247	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8239	Intermediate Similarity	NPD7473	Discontinued
0.8231	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8227	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8224	Intermediate Similarity	NPD6599	Discontinued
0.8224	Intermediate Similarity	NPD4380	Phase 2
0.8207	Intermediate Similarity	NPD1551	Phase 2
0.8194	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8194	Intermediate Similarity	NPD7768	Phase 2
0.8182	Intermediate Similarity	NPD230	Phase 1
0.8141	Intermediate Similarity	NPD3749	Approved
0.8129	Intermediate Similarity	NPD3817	Phase 2
0.8117	Intermediate Similarity	NPD6801	Discontinued
0.8077	Intermediate Similarity	NPD3882	Suspended
0.8067	Intermediate Similarity	NPD1511	Approved
0.8065	Intermediate Similarity	NPD2801	Approved
0.8063	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8041	Intermediate Similarity	NPD2800	Approved
0.8025	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD5844	Phase 1
0.8014	Intermediate Similarity	NPD3748	Approved
0.8013	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD6651	Approved
0.7987	Intermediate Similarity	NPD4628	Phase 3
0.7987	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7961	Intermediate Similarity	NPD1512	Approved
0.795	Intermediate Similarity	NPD6166	Phase 2
0.795	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.795	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7941	Intermediate Similarity	NPD9545	Approved
0.7919	Intermediate Similarity	NPD1243	Approved
0.7919	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7914	Intermediate Similarity	NPD9717	Approved
0.7891	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7866	Intermediate Similarity	NPD7074	Phase 3
0.7853	Intermediate Similarity	NPD3818	Discontinued
0.7838	Intermediate Similarity	NPD6099	Approved
0.7838	Intermediate Similarity	NPD6100	Approved
0.7834	Intermediate Similarity	NPD1465	Phase 2
0.7806	Intermediate Similarity	NPD3226	Approved
0.7805	Intermediate Similarity	NPD7054	Approved
0.7794	Intermediate Similarity	NPD9493	Approved
0.7792	Intermediate Similarity	NPD920	Approved
0.7792	Intermediate Similarity	NPD5403	Approved
0.7785	Intermediate Similarity	NPD5402	Approved
0.777	Intermediate Similarity	NPD2799	Discontinued
0.7763	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7758	Intermediate Similarity	NPD7472	Approved
0.7746	Intermediate Similarity	NPD1203	Approved
0.7725	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7724	Intermediate Similarity	NPD411	Approved
0.7714	Intermediate Similarity	NPD422	Phase 1
0.7712	Intermediate Similarity	NPD7390	Discontinued
0.7711	Intermediate Similarity	NPD5953	Discontinued
0.7711	Intermediate Similarity	NPD6797	Phase 2
0.7708	Intermediate Similarity	NPD6832	Phase 2
0.7702	Intermediate Similarity	NPD5494	Approved
0.7698	Intermediate Similarity	NPD4626	Approved
0.7697	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7687	Intermediate Similarity	NPD447	Suspended
0.7682	Intermediate Similarity	NPD2654	Approved
0.7667	Intermediate Similarity	NPD2346	Discontinued
0.7665	Intermediate Similarity	NPD6559	Discontinued
0.7665	Intermediate Similarity	NPD7251	Discontinued
0.7662	Intermediate Similarity	NPD5401	Approved
0.7662	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7662	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.766	Intermediate Similarity	NPD1608	Approved
0.7658	Intermediate Similarity	NPD37	Approved
0.7651	Intermediate Similarity	NPD7033	Discontinued
0.7651	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD6234	Discontinued
0.764	Intermediate Similarity	NPD919	Approved
0.7626	Intermediate Similarity	NPD5691	Approved
0.7625	Intermediate Similarity	NPD4965	Approved
0.7625	Intermediate Similarity	NPD4966	Approved
0.7625	Intermediate Similarity	NPD4967	Phase 2
0.7619	Intermediate Similarity	NPD7808	Phase 3
0.7619	Intermediate Similarity	NPD943	Approved
0.7605	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7603	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7603	Intermediate Similarity	NPD3764	Approved
0.76	Intermediate Similarity	NPD5404	Approved
0.76	Intermediate Similarity	NPD5408	Approved
0.76	Intermediate Similarity	NPD5406	Approved
0.76	Intermediate Similarity	NPD5405	Approved
0.759	Intermediate Similarity	NPD7286	Phase 2
0.758	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7572	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.755	Intermediate Similarity	NPD2344	Approved
0.7546	Intermediate Similarity	NPD7199	Phase 2
0.75	Intermediate Similarity	NPD7229	Phase 3
0.75	Intermediate Similarity	NPD2797	Approved
0.7484	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD3268	Approved
0.7466	Intermediate Similarity	NPD4908	Phase 1
0.7455	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD4288	Approved
0.745	Intermediate Similarity	NPD5124	Phase 1
0.745	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD2798	Approved
0.7448	Intermediate Similarity	NPD1019	Discontinued
0.7447	Intermediate Similarity	NPD1778	Approved
0.7447	Intermediate Similarity	NPD17	Approved
0.7431	Intermediate Similarity	NPD1283	Approved
0.7413	Intermediate Similarity	NPD9269	Phase 2
0.7412	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD7003	Approved
0.7389	Intermediate Similarity	NPD6273	Approved
0.7383	Intermediate Similarity	NPD4060	Phase 1
0.7376	Intermediate Similarity	NPD9268	Approved
0.7365	Intermediate Similarity	NPD2313	Discontinued
0.7365	Intermediate Similarity	NPD1296	Phase 2
0.7365	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7361	Intermediate Similarity	NPD4749	Approved
0.7356	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD2309	Approved
0.7349	Intermediate Similarity	NPD3926	Phase 2
0.7346	Intermediate Similarity	NPD5353	Approved
0.7343	Intermediate Similarity	NPD1610	Phase 2
0.7343	Intermediate Similarity	NPD1201	Approved
0.7333	Intermediate Similarity	NPD6355	Discontinued
0.7329	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD7228	Approved
0.732	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD6002	Phase 3
0.732	Intermediate Similarity	NPD6005	Phase 3
0.732	Intermediate Similarity	NPD6004	Phase 3
0.7303	Intermediate Similarity	NPD4308	Phase 3
0.7297	Intermediate Similarity	NPD3027	Phase 3
0.7297	Intermediate Similarity	NPD4625	Phase 3
0.7279	Intermediate Similarity	NPD9494	Approved
0.7273	Intermediate Similarity	NPD3496	Discontinued
0.7267	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD8312	Approved
0.7267	Intermediate Similarity	NPD8313	Approved
0.7267	Intermediate Similarity	NPD2979	Phase 3
0.726	Intermediate Similarity	NPD1470	Approved
0.726	Intermediate Similarity	NPD1164	Approved
0.7255	Intermediate Similarity	NPD4476	Approved
0.7255	Intermediate Similarity	NPD4477	Approved
0.7255	Intermediate Similarity	NPD2438	Suspended
0.7251	Intermediate Similarity	NPD3658	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD7458	Discontinued
0.7248	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD6798	Discontinued
0.7246	Intermediate Similarity	NPD5242	Approved
0.7243	Intermediate Similarity	NPD8151	Discontinued
0.7229	Intermediate Similarity	NPD1247	Approved
0.7222	Intermediate Similarity	NPD1281	Approved
0.7222	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD3751	Discontinued
0.7219	Intermediate Similarity	NPD7177	Discontinued
0.7206	Intermediate Similarity	NPD74	Approved
0.7206	Intermediate Similarity	NPD9266	Approved
0.7192	Intermediate Similarity	NPD3225	Approved
0.7186	Intermediate Similarity	NPD3787	Discontinued
0.7183	Intermediate Similarity	NPD1548	Phase 1
0.7172	Intermediate Similarity	NPD3972	Approved
0.7163	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD4287	Approved
0.7158	Intermediate Similarity	NPD7435	Discontinued
0.7152	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD1613	Approved
0.7143	Intermediate Similarity	NPD3267	Approved
0.7143	Intermediate Similarity	NPD3266	Approved
0.7143	Intermediate Similarity	NPD8150	Discontinued
0.7134	Intermediate Similarity	NPD6190	Approved
0.7132	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD9264	Approved
0.7132	Intermediate Similarity	NPD9267	Approved
0.7132	Intermediate Similarity	NPD9263	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