NPASS Compound

Structure

CID196197 OpenBabel06191715582D 22 25 0 0 1 0 0 0 0 0999 V2000 -1.5316 -0.8580 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8685 2.0695 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0633 -0.0001 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0001 -1.7687 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7658 -1.3265 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7659 1.3264 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2975 -0.4422 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0633 0.8842 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 0.8843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7659 -0.4422 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8843 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7659 -1.3265 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.2081 -0.5606 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5317 0.8843 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7658 -0.4422 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.8555 -0.5606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5317 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.2975 1.3264 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.0556 -1.1764 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2887 -0.0795 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7265 2.0694 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3 7 1 0 0 0 0 3 8 1 0 0 0 0 4 5 1 0 0 0 0 5 15 1 0 0 0 0 6 9 1 0 0 0 0 6 14 1 0 0 0 0 7 17 1 0 0 0 0 8 18 1 0 0 0 0 10 12 1 0 0 0 0 10 19 1 0 0 0 0 11 13 1 0 0 0 0 11 19 1 0 0 0 0 12 4 1 6 0 0 0 12 13 1 0 0 0 0 13 16 1 6 0 0 0 14 17 1 1 0 0 0 14 18 1 0 0 0 0 15 17 1 1 0 0 0 15 19 1 0 0 0 0 16 20 2 0 0 0 0 16 21 1 0 0 0 0 17 1 1 1 0 0 0 18 2 1 6 0 0 0 18 22 1 0 0 0 0 19 9 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	306.22
Volume:	326.689
LogP:	3.707
LogD:	2.847
LogS:	-4.089
# Rotatable Bonds:	1
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.773
Synthetic Accessibility Score:	5.606
Fsp3:	0.947
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:	-5.52
MDCK Permeability:	1.0287662007613108e-05
Pgp-inhibitor:	0.156
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.988

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.262
Plasma Protein Binding (PPB):	90.03943634033203%
Volume Distribution (VD):	0.66
Pgp-substrate:	9.287530899047852%

ADMET: Metabolism

CYP1A2-inhibitor:	0.013
CYP1A2-substrate:	0.598
CYP2C19-inhibitor:	0.015
CYP2C19-substrate:	0.792
CYP2C9-inhibitor:	0.053
CYP2C9-substrate:	0.502
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.175
CYP3A4-inhibitor:	0.185
CYP3A4-substrate:	0.056

ADMET: Excretion

Clearance (CL):	4.471
Half-life (T1/2):	0.645

ADMET: Toxicity

hERG Blockers:	0.03
Human Hepatotoxicity (H-HT):	0.55
Drug-inuced Liver Injury (DILI):	0.044
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.059
Maximum Recommended Daily Dose:	0.624
Skin Sensitization:	0.848
Carcinogencity:	0.437
Eye Corrosion:	0.014
Eye Irritation:	0.202
Respiratory Toxicity:	0.945

Download Data

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

Natural Product: NPC196197

Natural Product ID:	NPC196197
*Common Name:**	RLNDAGRLPOJRPI-ANXUHKRASA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	RLNDAGRLPOJRPI-ANXUHKRASA-N
Standard InCHI:	InChI=1S/C19H30O3/c1-17-7-3-8-18(2,22)14(17)6-9-19-10-12(4-5-15(17)19)13(11-19)16(20)21/h12-15,22H,3-11H2,1-2H3,(H,20,21)/t12-,13+,14+,15+,17-,18-,19+/m1/s1
SMILES:	C[C@@]12CCC[C@](C)([C@H]1CC[C@]13C[C@@H](CC[C@@H]23)[C@H](C1)C(=O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL483432
PubChem CID:	3001698
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0003782] Kaurane diterpenoids

*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
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	seeds	n.a.	n.a.	PMID[11141125]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12398544]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18419154]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19296389]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21910504]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	seeds	n.a.	n.a.	PMID[22011319]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	seed	n.a.	PMID[22011319]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	Barks	n.a.	n.a.	PMID[2348205]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	fruit	n.a.	PMID[8786370]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	bark	n.a.	n.a.	PMID[9214729]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2884	Annona squamosa	Species	Annonaceae	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	4

Activity Type	# Activity
NON-MOLECULAR	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	4.5	%	PMID[476284]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	30.5	%	PMID[476284]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	13.3	%	PMID[476284]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	2.0	%	PMID[476284]

☑ 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 NPC196197 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	294
0.1-0.2	3400
0.2-0.3	16344
0.3-0.4	8640
0.4-0.5	5691
0.5-0.6	5080
0.6-0.7	2554
0.7-0.8	551
0.8-0.85	86
0.85-0.9	42
0.9-0.95	14
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9231	High Similarity	NPC477931
0.9231	High Similarity	NPC42060
0.9231	High Similarity	NPC268736
0.9091	High Similarity	NPC474221
0.9091	High Similarity	NPC130459
0.9091	High Similarity	NPC478180
0.9	High Similarity	NPC212733
0.8971	High Similarity	NPC108131
0.8873	High Similarity	NPC4209
0.8857	High Similarity	NPC280026
0.8857	High Similarity	NPC167702
0.8824	High Similarity	NPC474962
0.8824	High Similarity	NPC252032
0.8824	High Similarity	NPC64466
0.8824	High Similarity	NPC476734
0.8824	High Similarity	NPC469941
0.8824	High Similarity	NPC319671
0.8788	High Similarity	NPC19311
0.8788	High Similarity	NPC230047
0.875	High Similarity	NPC143133
0.875	High Similarity	NPC298168
0.875	High Similarity	NPC317913
0.875	High Similarity	NPC207010
0.8696	High Similarity	NPC477850
0.8696	High Similarity	NPC477929
0.8676	High Similarity	NPC473225
0.863	High Similarity	NPC171426
0.863	High Similarity	NPC224802
0.863	High Similarity	NPC34046
0.863	High Similarity	NPC324700
0.863	High Similarity	NPC80089
0.8571	High Similarity	NPC472309
0.8571	High Similarity	NPC469940
0.8533	High Similarity	NPC12933
0.8533	High Similarity	NPC58631
0.8529	High Similarity	NPC41542
0.8514	High Similarity	NPC201276
0.8514	High Similarity	NPC80891
0.8514	High Similarity	NPC320144
0.8493	Intermediate Similarity	NPC477919
0.8493	Intermediate Similarity	NPC66105
0.8493	Intermediate Similarity	NPC474404
0.8493	Intermediate Similarity	NPC180199
0.8472	Intermediate Similarity	NPC472311
0.8451	Intermediate Similarity	NPC232112
0.84	Intermediate Similarity	NPC261616
0.84	Intermediate Similarity	NPC477851
0.8378	Intermediate Similarity	NPC199965
0.8378	Intermediate Similarity	NPC329117
0.8378	Intermediate Similarity	NPC185465
0.8378	Intermediate Similarity	NPC476732
0.8333	Intermediate Similarity	NPC477930
0.831	Intermediate Similarity	NPC320549
0.831	Intermediate Similarity	NPC156277
0.831	Intermediate Similarity	NPC58057
0.831	Intermediate Similarity	NPC151018
0.831	Intermediate Similarity	NPC89310
0.831	Intermediate Similarity	NPC197701
0.8286	Intermediate Similarity	NPC327728
0.8286	Intermediate Similarity	NPC6120
0.8286	Intermediate Similarity	NPC131892
0.8286	Intermediate Similarity	NPC213178
0.8243	Intermediate Similarity	NPC475031
0.8243	Intermediate Similarity	NPC477918
0.8243	Intermediate Similarity	NPC23884
0.8219	Intermediate Similarity	NPC174964
0.8219	Intermediate Similarity	NPC125767
0.8219	Intermediate Similarity	NPC477934
0.8219	Intermediate Similarity	NPC195155
0.8219	Intermediate Similarity	NPC21220
0.8219	Intermediate Similarity	NPC97534
0.8219	Intermediate Similarity	NPC273366
0.8194	Intermediate Similarity	NPC161187
0.8194	Intermediate Similarity	NPC330659
0.8194	Intermediate Similarity	NPC244708
0.8182	Intermediate Similarity	NPC61107
0.8182	Intermediate Similarity	NPC289486
0.8182	Intermediate Similarity	NPC30583
0.8182	Intermediate Similarity	NPC121121
0.8158	Intermediate Similarity	NPC472853
0.8143	Intermediate Similarity	NPC100917
0.8143	Intermediate Similarity	NPC281203
0.8143	Intermediate Similarity	NPC469724
0.8143	Intermediate Similarity	NPC31187
0.8143	Intermediate Similarity	NPC470956
0.8116	Intermediate Similarity	NPC84562
0.8108	Intermediate Similarity	NPC477932
0.8108	Intermediate Similarity	NPC246445
0.8108	Intermediate Similarity	NPC475742
0.8108	Intermediate Similarity	NPC104806
0.8108	Intermediate Similarity	NPC472487
0.8108	Intermediate Similarity	NPC472486
0.8108	Intermediate Similarity	NPC477933
0.8108	Intermediate Similarity	NPC5767
0.8082	Intermediate Similarity	NPC472854
0.8082	Intermediate Similarity	NPC254340
0.8056	Intermediate Similarity	NPC473267
0.8028	Intermediate Similarity	NPC324607
0.8028	Intermediate Similarity	NPC321732
0.8026	Intermediate Similarity	NPC192744
0.8	Intermediate Similarity	NPC212661
0.8	Intermediate Similarity	NPC68828
0.8	Intermediate Similarity	NPC472272
0.8	Intermediate Similarity	NPC221420
0.8	Intermediate Similarity	NPC471035
0.7975	Intermediate Similarity	NPC473336
0.7975	Intermediate Similarity	NPC319909
0.7975	Intermediate Similarity	NPC471044
0.7973	Intermediate Similarity	NPC27349
0.7973	Intermediate Similarity	NPC159789
0.7973	Intermediate Similarity	NPC155441
0.7973	Intermediate Similarity	NPC24014
0.7971	Intermediate Similarity	NPC469791
0.7949	Intermediate Similarity	NPC477935
0.7949	Intermediate Similarity	NPC477936
0.7945	Intermediate Similarity	NPC310766
0.7917	Intermediate Similarity	NPC476731
0.7895	Intermediate Similarity	NPC321690
0.7875	Intermediate Similarity	NPC294438
0.7875	Intermediate Similarity	NPC264317
0.7867	Intermediate Similarity	NPC471046
0.7848	Intermediate Similarity	NPC259173
0.7848	Intermediate Similarity	NPC471037
0.7838	Intermediate Similarity	NPC133922
0.7826	Intermediate Similarity	NPC128608
0.7821	Intermediate Similarity	NPC280781
0.7821	Intermediate Similarity	NPC48756
0.7808	Intermediate Similarity	NPC247195
0.7808	Intermediate Similarity	NPC478227
0.7792	Intermediate Similarity	NPC472310
0.7778	Intermediate Similarity	NPC12774
0.7778	Intermediate Similarity	NPC2783
0.7778	Intermediate Similarity	NPC302111
0.7763	Intermediate Similarity	NPC112463
0.7763	Intermediate Similarity	NPC264602
0.7763	Intermediate Similarity	NPC212453
0.7763	Intermediate Similarity	NPC171658
0.7733	Intermediate Similarity	NPC72444
0.7722	Intermediate Similarity	NPC268040
0.7722	Intermediate Similarity	NPC13494
0.7711	Intermediate Similarity	NPC24705
0.7711	Intermediate Similarity	NPC56962
0.7703	Intermediate Similarity	NPC81759
0.7683	Intermediate Similarity	NPC269360
0.7683	Intermediate Similarity	NPC264005
0.7683	Intermediate Similarity	NPC252714
0.7683	Intermediate Similarity	NPC33768
0.7662	Intermediate Similarity	NPC472608
0.7662	Intermediate Similarity	NPC471045
0.7662	Intermediate Similarity	NPC243594
0.7662	Intermediate Similarity	NPC31031
0.7647	Intermediate Similarity	NPC478126
0.7639	Intermediate Similarity	NPC475977
0.7632	Intermediate Similarity	NPC20466
0.7625	Intermediate Similarity	NPC245866
0.7625	Intermediate Similarity	NPC327451
0.7625	Intermediate Similarity	NPC477852
0.7625	Intermediate Similarity	NPC472740
0.7612	Intermediate Similarity	NPC162685
0.76	Intermediate Similarity	NPC38426
0.76	Intermediate Similarity	NPC162164
0.76	Intermediate Similarity	NPC96759
0.7595	Intermediate Similarity	NPC469745
0.7595	Intermediate Similarity	NPC271572
0.7595	Intermediate Similarity	NPC147066
0.7595	Intermediate Similarity	NPC232625
0.7595	Intermediate Similarity	NPC474870
0.7595	Intermediate Similarity	NPC476071
0.759	Intermediate Similarity	NPC471900
0.759	Intermediate Similarity	NPC146937
0.759	Intermediate Similarity	NPC4309
0.759	Intermediate Similarity	NPC474719
0.759	Intermediate Similarity	NPC16377
0.7576	Intermediate Similarity	NPC143597
0.7576	Intermediate Similarity	NPC151464
0.7576	Intermediate Similarity	NPC3025
0.7568	Intermediate Similarity	NPC126642
0.7564	Intermediate Similarity	NPC220379
0.7564	Intermediate Similarity	NPC245029
0.7564	Intermediate Similarity	NPC31302
0.7564	Intermediate Similarity	NPC215843
0.7564	Intermediate Similarity	NPC476176
0.7561	Intermediate Similarity	NPC92139
0.7538	Intermediate Similarity	NPC53245
0.7538	Intermediate Similarity	NPC288296
0.7532	Intermediate Similarity	NPC471151
0.7532	Intermediate Similarity	NPC307865
0.7531	Intermediate Similarity	NPC50438
0.7531	Intermediate Similarity	NPC474996
0.75	Intermediate Similarity	NPC317066
0.75	Intermediate Similarity	NPC220498
0.75	Intermediate Similarity	NPC311642
0.75	Intermediate Similarity	NPC100366
0.75	Intermediate Similarity	NPC48079
0.75	Intermediate Similarity	NPC258153
0.75	Intermediate Similarity	NPC201027
0.75	Intermediate Similarity	NPC63190
0.75	Intermediate Similarity	NPC476458
0.75	Intermediate Similarity	NPC95958
0.75	Intermediate Similarity	NPC102156

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 NPC196197 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	352
0.1-0.2	3589
0.2-0.3	3644
0.3-0.4	936
0.4-0.5	240
0.5-0.6	227
0.6-0.7	128
0.7-0.8	9
0.8-0.85	10
0.85-0.9	9
0.9-0.95	6
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9231	High Similarity	NPD4224	Phase 2
0.8955	High Similarity	NPD5361	Clinical (unspecified phase)
0.8955	High Similarity	NPD5360	Phase 3
0.8873	High Similarity	NPD6117	Approved
0.8857	High Similarity	NPD6113	Clinical (unspecified phase)
0.8841	High Similarity	NPD6081	Approved
0.875	High Similarity	NPD6116	Phase 1
0.863	High Similarity	NPD6114	Approved
0.863	High Similarity	NPD6697	Approved
0.863	High Similarity	NPD6118	Approved
0.863	High Similarity	NPD6115	Approved
0.8571	High Similarity	NPD4758	Discontinued
0.8472	Intermediate Similarity	NPD3702	Approved
0.831	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.831	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.8286	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.8286	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.8235	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.8169	Intermediate Similarity	NPD4789	Approved
0.8028	Intermediate Similarity	NPD3698	Phase 2
0.7973	Intermediate Similarity	NPD3703	Phase 2
0.7917	Intermediate Similarity	NPD4244	Approved
0.7917	Intermediate Similarity	NPD4245	Approved
0.7895	Intermediate Similarity	NPD5364	Discontinued
0.7875	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7808	Intermediate Similarity	NPD5777	Approved
0.7436	Intermediate Similarity	NPD3671	Phase 1
0.7326	Intermediate Similarity	NPD8034	Phase 2
0.7326	Intermediate Similarity	NPD8035	Phase 2
0.7297	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD4788	Approved
0.7073	Intermediate Similarity	NPD4223	Phase 3
0.7073	Intermediate Similarity	NPD4221	Approved
0.7015	Intermediate Similarity	NPD615	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3617	Approved
0.6974	Remote Similarity	NPD4787	Phase 1
0.6951	Remote Similarity	NPD4692	Approved
0.6951	Remote Similarity	NPD4139	Approved
0.6941	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD4197	Approved
0.6824	Remote Similarity	NPD5329	Approved
0.6774	Remote Similarity	NPD8418	Phase 2
0.6761	Remote Similarity	NPD3198	Approved
0.6744	Remote Similarity	NPD4138	Approved
0.6744	Remote Similarity	NPD5205	Approved
0.6744	Remote Similarity	NPD4690	Approved
0.6744	Remote Similarity	NPD4689	Approved
0.6744	Remote Similarity	NPD3618	Phase 1
0.6744	Remote Similarity	NPD6098	Approved
0.6744	Remote Similarity	NPD4688	Approved
0.6744	Remote Similarity	NPD4693	Phase 3
0.6742	Remote Similarity	NPD5284	Approved
0.6742	Remote Similarity	NPD5281	Approved
0.6706	Remote Similarity	NPD4786	Approved
0.6705	Remote Similarity	NPD5328	Approved
0.6667	Remote Similarity	NPD6399	Phase 3
0.6667	Remote Similarity	NPD4202	Approved
0.6667	Remote Similarity	NPD3667	Approved
0.6593	Remote Similarity	NPD6001	Approved
0.6591	Remote Similarity	NPD5208	Approved
0.6562	Remote Similarity	NPD634	Phase 3
0.6559	Remote Similarity	NPD6084	Phase 2
0.6559	Remote Similarity	NPD6083	Phase 2
0.6556	Remote Similarity	NPD7515	Phase 2
0.6556	Remote Similarity	NPD6079	Approved
0.6552	Remote Similarity	NPD5690	Phase 2
0.6552	Remote Similarity	NPD5280	Approved
0.6552	Remote Similarity	NPD4694	Approved
0.6522	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD5695	Phase 3
0.6517	Remote Similarity	NPD6673	Approved
0.6517	Remote Similarity	NPD6080	Approved
0.6517	Remote Similarity	NPD4753	Phase 2
0.6517	Remote Similarity	NPD6904	Approved
0.6512	Remote Similarity	NPD3666	Approved
0.6512	Remote Similarity	NPD3665	Phase 1
0.6512	Remote Similarity	NPD3133	Approved
0.6489	Remote Similarity	NPD5696	Approved
0.6447	Remote Similarity	NPD375	Phase 2
0.6429	Remote Similarity	NPD6402	Approved
0.6429	Remote Similarity	NPD6675	Approved
0.6429	Remote Similarity	NPD5739	Approved
0.6429	Remote Similarity	NPD7128	Approved
0.6429	Remote Similarity	NPD7525	Registered
0.6413	Remote Similarity	NPD7748	Approved
0.6404	Remote Similarity	NPD5737	Approved
0.6404	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD6672	Approved
0.6383	Remote Similarity	NPD4755	Approved
0.6374	Remote Similarity	NPD5693	Phase 1
0.6364	Remote Similarity	NPD6409	Approved
0.6364	Remote Similarity	NPD5330	Approved
0.6364	Remote Similarity	NPD5697	Approved
0.6364	Remote Similarity	NPD7521	Approved
0.6364	Remote Similarity	NPD6684	Approved
0.6364	Remote Similarity	NPD7334	Approved
0.6364	Remote Similarity	NPD7146	Approved
0.6364	Remote Similarity	NPD5701	Approved
0.6333	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD7638	Approved
0.631	Remote Similarity	NPD4195	Approved
0.63	Remote Similarity	NPD6011	Approved
0.63	Remote Similarity	NPD6881	Approved
0.63	Remote Similarity	NPD6899	Approved
0.63	Remote Similarity	NPD7320	Approved
0.6292	Remote Similarity	NPD3573	Approved
0.6286	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.6277	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6277	Remote Similarity	NPD4697	Phase 3
0.6277	Remote Similarity	NPD5221	Approved
0.6277	Remote Similarity	NPD5222	Approved
0.6264	Remote Similarity	NPD5692	Phase 3
0.6264	Remote Similarity	NPD5207	Approved
0.625	Remote Similarity	NPD4243	Approved
0.625	Remote Similarity	NPD5286	Approved
0.625	Remote Similarity	NPD4700	Approved
0.625	Remote Similarity	NPD5285	Approved
0.625	Remote Similarity	NPD7639	Approved
0.625	Remote Similarity	NPD4696	Approved
0.625	Remote Similarity	NPD7640	Approved
0.6238	Remote Similarity	NPD6012	Approved
0.6238	Remote Similarity	NPD6014	Approved
0.6238	Remote Similarity	NPD6373	Approved
0.6238	Remote Similarity	NPD6372	Approved
0.6238	Remote Similarity	NPD6013	Approved
0.6235	Remote Similarity	NPD6928	Phase 2
0.6232	Remote Similarity	NPD3186	Phase 1
0.6222	Remote Similarity	NPD6903	Approved
0.6211	Remote Similarity	NPD5173	Approved
0.6211	Remote Similarity	NPD7902	Approved
0.6196	Remote Similarity	NPD5694	Approved
0.6196	Remote Similarity	NPD6050	Approved
0.6186	Remote Similarity	NPD5223	Approved
0.618	Remote Similarity	NPD4519	Discontinued
0.618	Remote Similarity	NPD4623	Approved
0.618	Remote Similarity	NPD5279	Phase 3
0.6176	Remote Similarity	NPD7290	Approved
0.6176	Remote Similarity	NPD7102	Approved
0.6176	Remote Similarity	NPD6883	Approved
0.617	Remote Similarity	NPD4629	Approved
0.617	Remote Similarity	NPD5210	Approved
0.6136	Remote Similarity	NPD3668	Phase 3
0.6129	Remote Similarity	NPD5133	Approved
0.6125	Remote Similarity	NPD4747	Approved
0.6122	Remote Similarity	NPD5224	Approved
0.6122	Remote Similarity	NPD4633	Approved
0.6122	Remote Similarity	NPD5211	Phase 2
0.6122	Remote Similarity	NPD5226	Approved
0.6122	Remote Similarity	NPD7632	Discontinued
0.6122	Remote Similarity	NPD5225	Approved
0.6117	Remote Similarity	NPD6847	Approved
0.6117	Remote Similarity	NPD6649	Approved
0.6117	Remote Similarity	NPD6869	Approved
0.6117	Remote Similarity	NPD6617	Approved
0.6117	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6117	Remote Similarity	NPD6650	Approved
0.6117	Remote Similarity	NPD8130	Phase 1
0.6098	Remote Similarity	NPD4784	Approved
0.6098	Remote Similarity	NPD4785	Approved
0.6094	Remote Similarity	NPD387	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD4096	Approved
0.6076	Remote Similarity	NPD6705	Phase 1
0.6061	Remote Similarity	NPD5174	Approved
0.6061	Remote Similarity	NPD4754	Approved
0.6061	Remote Similarity	NPD5175	Approved
0.6058	Remote Similarity	NPD6882	Approved
0.6058	Remote Similarity	NPD8297	Approved
0.6047	Remote Similarity	NPD4695	Discontinued
0.6024	Remote Similarity	NPD5275	Approved
0.6024	Remote Similarity	NPD4190	Phase 3
0.6023	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6023	Remote Similarity	NPD3669	Approved
0.602	Remote Similarity	NPD1700	Approved
0.6	Remote Similarity	NPD4632	Approved
0.6	Remote Similarity	NPD5654	Approved
0.6	Remote Similarity	NPD4137	Phase 3
0.6	Remote Similarity	NPD8298	Phase 2
0.6	Remote Similarity	NPD5141	Approved
0.6	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.5977	Remote Similarity	NPD1780	Approved
0.5977	Remote Similarity	NPD1779	Approved
0.597	Remote Similarity	NPD344	Approved
0.597	Remote Similarity	NPD343	Approved
0.597	Remote Similarity	NPD345	Approved
0.5941	Remote Similarity	NPD4768	Approved
0.5941	Remote Similarity	NPD6920	Discontinued
0.5941	Remote Similarity	NPD6008	Approved
0.5941	Remote Similarity	NPD4767	Approved
0.5938	Remote Similarity	NPD7614	Phase 1
0.5926	Remote Similarity	NPD4691	Approved
0.5918	Remote Similarity	NPD6404	Discontinued
0.5895	Remote Similarity	NPD7900	Approved
0.5895	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5888	Remote Similarity	NPD6274	Approved
0.5876	Remote Similarity	NPD5959	Approved
0.5875	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.587	Remote Similarity	NPD4518	Approved
0.5862	Remote Similarity	NPD4748	Discontinued
0.5849	Remote Similarity	NPD8133	Approved
0.5833	Remote Similarity	NPD6317	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