NPASS Compound

Structure

NPC224455 OpenBabel07101718292D 22 23 0 0 1 0 0 0 0 0999 V2000 -2.5981 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 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 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 -0.8660 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 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 -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 0 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 1.7321 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 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 -0.8660 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 4.5000 0.0000 C 0 0 0 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 2.5981 -2.5000 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 0.0000 5.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 5.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 11 1 0 0 0 0 3 4 1 0 0 0 0 3 5 2 0 0 0 0 4 6 2 0 0 0 0 6 17 1 0 0 0 0 7 12 1 0 0 0 0 7 13 1 0 0 0 0 8 11 2 0 0 0 0 8 16 1 0 0 0 0 9 13 1 0 0 0 0 10 19 1 0 0 0 0 11 14 1 0 0 0 0 12 2 1 6 0 0 0 12 18 1 0 0 0 0 13 10 1 6 0 0 0 14 5 1 6 0 0 0 14 18 1 0 0 0 0 15 9 1 6 0 0 0 15 16 1 0 0 0 0 15 18 1 0 0 0 0 16 20 1 1 0 0 0 17 21 2 0 0 0 0 17 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	306.18
Volume:	327.386
LogP:	2.324
LogD:	1.147
LogS:	-2.137
# Rotatable Bonds:	4
TPSA:	77.76
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.746
Synthetic Accessibility Score:	4.816
Fsp3:	0.611
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.987
MDCK Permeability:	1.4448775800701696e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.072
Human Intestinal Absorption (HIA):	0.872
20% Bioavailability (F20%):	0.071
30% Bioavailability (F30%):	0.006

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.763
Plasma Protein Binding (PPB):	78.53934478759766%
Volume Distribution (VD):	0.434
Pgp-substrate:	19.213441848754883%

ADMET: Metabolism

CYP1A2-inhibitor:	0.088
CYP1A2-substrate:	0.103
CYP2C19-inhibitor:	0.021
CYP2C19-substrate:	0.538
CYP2C9-inhibitor:	0.027
CYP2C9-substrate:	0.946
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.139
CYP3A4-inhibitor:	0.026
CYP3A4-substrate:	0.138

ADMET: Excretion

Clearance (CL):	3.522
Half-life (T1/2):	0.916

ADMET: Toxicity

hERG Blockers:	0.065
Human Hepatotoxicity (H-HT):	0.819
Drug-inuced Liver Injury (DILI):	0.034
AMES Toxicity:	0.031
Rat Oral Acute Toxicity:	0.784
Maximum Recommended Daily Dose:	0.941
Skin Sensitization:	0.961
Carcinogencity:	0.646
Eye Corrosion:	0.005
Eye Irritation:	0.186
Respiratory Toxicity:	0.949

Download Data

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

Natural Product: NPC224455

Natural Product ID:	NPC224455
*Common Name:**	Tanzawaic Acid H
IUPAC Name:	(2E,4E)-5-[(1R,4R,4aS,6S,8R,8aR)-4-hydroxy-6-(hydroxymethyl)-2,8-dimethyl-1,4,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]penta-2,4-dienoic acid
Synonyms:
Standard InCHIKey:	KUVSXNIEVWRYCQ-PIOYMUNPSA-N
Standard InCHI:	InChI=1S/C18H26O4/c1-11-8-16(20)15-9-13(10-19)7-12(2)18(15)14(11)5-3-4-6-17(21)22/h3-6,8,12-16,18-20H,7,9-10H2,1-2H3,(H,21,22)/b5-3+,6-4+/t12-,13+,14+,15-,16+,18-/m1/s1
SMILES:	CC1=C[C@@H]([C@H]2C[C@H](C[C@@H](C)[C@@H]2[C@H]1/C=C/C=C/C(=O)O)CO)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2385863
PubChem CID:	71726409
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0000262] Fatty acids and conjugates [CHEMONTID:0003086] Medium-chain fatty acids

*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
NPO19366	Penicillium citrinum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15730261]
NPO19366	Penicillium citrinum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15973055]
NPO19366	Penicillium citrinum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18656987]
NPO19366	Penicillium citrinum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21053938]
NPO19366	Penicillium citrinum	Species	Aspergillaceae	Eukaryota	n.a.	Moroccan	n.a.	PMID[23713692]
NPO19366	Penicillium citrinum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26295595]
NPO19366	Penicillium citrinum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7766039]
NPO19366	Penicillium citrinum	Species	Aspergillaceae	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
IC50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1864	Cell Line	L5178Y	Mus musculus	IC50	>	10000.0	nM	PMID[454411]

☑ 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 NPC224455 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	162
0.1-0.2	876
0.2-0.3	4162
0.3-0.4	10348
0.4-0.5	13606
0.5-0.6	8010
0.6-0.7	4690
0.7-0.8	792
0.8-0.85	30
0.85-0.9	13
0.9-0.95	7
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.925	High Similarity	NPC302360
0.9125	High Similarity	NPC57370
0.8902	High Similarity	NPC109528
0.881	High Similarity	NPC229612
0.881	High Similarity	NPC7280
0.8488	Intermediate Similarity	NPC314727
0.8444	Intermediate Similarity	NPC99726
0.8434	Intermediate Similarity	NPC79945
0.8315	Intermediate Similarity	NPC469491
0.8293	Intermediate Similarity	NPC271104
0.8276	Intermediate Similarity	NPC16265
0.8202	Intermediate Similarity	NPC214697
0.8193	Intermediate Similarity	NPC6663
0.8111	Intermediate Similarity	NPC279410
0.8111	Intermediate Similarity	NPC119562
0.8095	Intermediate Similarity	NPC2524
0.8095	Intermediate Similarity	NPC256112
0.809	Intermediate Similarity	NPC212948
0.8072	Intermediate Similarity	NPC281880
0.8049	Intermediate Similarity	NPC172066
0.8026	Intermediate Similarity	NPC255781
0.7978	Intermediate Similarity	NPC182136
0.7976	Intermediate Similarity	NPC159148
0.7975	Intermediate Similarity	NPC95863
0.7955	Intermediate Similarity	NPC193843
0.7955	Intermediate Similarity	NPC291665
0.7955	Intermediate Similarity	NPC249889
0.7952	Intermediate Similarity	NPC242767
0.7935	Intermediate Similarity	NPC250757
0.7935	Intermediate Similarity	NPC301534
0.7935	Intermediate Similarity	NPC190713
0.7931	Intermediate Similarity	NPC175145
0.7931	Intermediate Similarity	NPC475069
0.7907	Intermediate Similarity	NPC102048
0.7865	Intermediate Similarity	NPC118011
0.7865	Intermediate Similarity	NPC472240
0.7865	Intermediate Similarity	NPC146554
0.7865	Intermediate Similarity	NPC36668
0.7865	Intermediate Similarity	NPC262858
0.7865	Intermediate Similarity	NPC470734
0.7865	Intermediate Similarity	NPC310236
0.7849	Intermediate Similarity	NPC98112
0.7849	Intermediate Similarity	NPC141401
0.7848	Intermediate Similarity	NPC34834
0.7841	Intermediate Similarity	NPC471796
0.7841	Intermediate Similarity	NPC313658
0.7841	Intermediate Similarity	NPC316138
0.7805	Intermediate Similarity	NPC253190
0.7802	Intermediate Similarity	NPC152778
0.7802	Intermediate Similarity	NPC162615
0.7802	Intermediate Similarity	NPC205034
0.7792	Intermediate Similarity	NPC202017
0.7791	Intermediate Similarity	NPC311070
0.7791	Intermediate Similarity	NPC476927
0.7778	Intermediate Similarity	NPC310479
0.7766	Intermediate Similarity	NPC235464
0.7766	Intermediate Similarity	NPC166745
0.7765	Intermediate Similarity	NPC315731
0.7765	Intermediate Similarity	NPC170303
0.7753	Intermediate Similarity	NPC72397
0.7753	Intermediate Similarity	NPC104560
0.7742	Intermediate Similarity	NPC473153
0.7727	Intermediate Similarity	NPC194417
0.7727	Intermediate Similarity	NPC473226
0.7727	Intermediate Similarity	NPC471219
0.7727	Intermediate Similarity	NPC82979
0.7722	Intermediate Similarity	NPC471560
0.7717	Intermediate Similarity	NPC57117
0.7717	Intermediate Similarity	NPC470255
0.7717	Intermediate Similarity	NPC191521
0.7711	Intermediate Similarity	NPC132542
0.7711	Intermediate Similarity	NPC40049
0.7692	Intermediate Similarity	NPC142838
0.7692	Intermediate Similarity	NPC474018
0.7692	Intermediate Similarity	NPC473986
0.7692	Intermediate Similarity	NPC473675
0.7677	Intermediate Similarity	NPC470024
0.7667	Intermediate Similarity	NPC246028
0.7667	Intermediate Similarity	NPC5509
0.766	Intermediate Similarity	NPC208094
0.7654	Intermediate Similarity	NPC35656
0.7654	Intermediate Similarity	NPC130665
0.7653	Intermediate Similarity	NPC172867
0.764	Intermediate Similarity	NPC199382
0.7629	Intermediate Similarity	NPC85742
0.7619	Intermediate Similarity	NPC198240
0.7614	Intermediate Similarity	NPC42586
0.7614	Intermediate Similarity	NPC471795
0.7614	Intermediate Similarity	NPC473251
0.7614	Intermediate Similarity	NPC476426
0.7609	Intermediate Similarity	NPC476304
0.7609	Intermediate Similarity	NPC115021
0.7609	Intermediate Similarity	NPC476049
0.7609	Intermediate Similarity	NPC38232
0.7604	Intermediate Similarity	NPC282524
0.7604	Intermediate Similarity	NPC472924
0.7595	Intermediate Similarity	NPC117804
0.759	Intermediate Similarity	NPC250621
0.7586	Intermediate Similarity	NPC474789
0.7586	Intermediate Similarity	NPC23748
0.7586	Intermediate Similarity	NPC52108
0.7586	Intermediate Similarity	NPC97913
0.7586	Intermediate Similarity	NPC297398
0.7586	Intermediate Similarity	NPC49019
0.7582	Intermediate Similarity	NPC78973
0.7582	Intermediate Similarity	NPC19771
0.7582	Intermediate Similarity	NPC221111
0.7582	Intermediate Similarity	NPC469403
0.7582	Intermediate Similarity	NPC280149
0.7582	Intermediate Similarity	NPC220216
0.7582	Intermediate Similarity	NPC48732
0.7579	Intermediate Similarity	NPC92275
0.7579	Intermediate Similarity	NPC103051
0.7579	Intermediate Similarity	NPC471717
0.7579	Intermediate Similarity	NPC23364
0.7579	Intermediate Similarity	NPC57079
0.7579	Intermediate Similarity	NPC108368
0.7579	Intermediate Similarity	NPC218107
0.7579	Intermediate Similarity	NPC278673
0.7576	Intermediate Similarity	NPC109376
0.7561	Intermediate Similarity	NPC306727
0.7558	Intermediate Similarity	NPC184208
0.7558	Intermediate Similarity	NPC8538
0.7558	Intermediate Similarity	NPC6434
0.7558	Intermediate Similarity	NPC476646
0.7556	Intermediate Similarity	NPC473229
0.7556	Intermediate Similarity	NPC472810
0.7556	Intermediate Similarity	NPC472809
0.7553	Intermediate Similarity	NPC456
0.7553	Intermediate Similarity	NPC202833
0.7553	Intermediate Similarity	NPC57664
0.7553	Intermediate Similarity	NPC134072
0.7553	Intermediate Similarity	NPC472941
0.7553	Intermediate Similarity	NPC16967
0.7553	Intermediate Similarity	NPC234993
0.7551	Intermediate Similarity	NPC200861
0.7531	Intermediate Similarity	NPC23954
0.7529	Intermediate Similarity	NPC139712
0.7529	Intermediate Similarity	NPC100906
0.7529	Intermediate Similarity	NPC308038
0.7529	Intermediate Similarity	NPC55304
0.7529	Intermediate Similarity	NPC226226
0.7528	Intermediate Similarity	NPC472986
0.7528	Intermediate Similarity	NPC131813
0.7528	Intermediate Similarity	NPC322159
0.7528	Intermediate Similarity	NPC472985
0.7527	Intermediate Similarity	NPC105490
0.7527	Intermediate Similarity	NPC474922
0.7527	Intermediate Similarity	NPC104925
0.7527	Intermediate Similarity	NPC298973
0.7527	Intermediate Similarity	NPC299100
0.7527	Intermediate Similarity	NPC476186
0.7527	Intermediate Similarity	NPC469406
0.7526	Intermediate Similarity	NPC11956
0.7526	Intermediate Similarity	NPC31058
0.7526	Intermediate Similarity	NPC293753
0.7526	Intermediate Similarity	NPC273005
0.7526	Intermediate Similarity	NPC469606
0.75	Intermediate Similarity	NPC124374
0.75	Intermediate Similarity	NPC474248
0.75	Intermediate Similarity	NPC61952
0.75	Intermediate Similarity	NPC477574
0.75	Intermediate Similarity	NPC266955
0.75	Intermediate Similarity	NPC97377
0.75	Intermediate Similarity	NPC306951
0.75	Intermediate Similarity	NPC204341
0.75	Intermediate Similarity	NPC164577
0.75	Intermediate Similarity	NPC472865
0.75	Intermediate Similarity	NPC224660
0.75	Intermediate Similarity	NPC165064
0.75	Intermediate Similarity	NPC227865
0.75	Intermediate Similarity	NPC203403
0.75	Intermediate Similarity	NPC110923
0.75	Intermediate Similarity	NPC91594
0.75	Intermediate Similarity	NPC234335
0.75	Intermediate Similarity	NPC315394
0.75	Intermediate Similarity	NPC283619
0.75	Intermediate Similarity	NPC470074
0.75	Intermediate Similarity	NPC74296
0.7475	Intermediate Similarity	NPC218158
0.7474	Intermediate Similarity	NPC477719
0.7474	Intermediate Similarity	NPC202705
0.7474	Intermediate Similarity	NPC287668
0.7474	Intermediate Similarity	NPC477718
0.7474	Intermediate Similarity	NPC320306
0.7474	Intermediate Similarity	NPC108078
0.7473	Intermediate Similarity	NPC261320
0.7473	Intermediate Similarity	NPC50488
0.7473	Intermediate Similarity	NPC281524
0.7473	Intermediate Similarity	NPC170633
0.7473	Intermediate Similarity	NPC82876
0.7473	Intermediate Similarity	NPC474396
0.7473	Intermediate Similarity	NPC212598
0.7473	Intermediate Similarity	NPC214387
0.7473	Intermediate Similarity	NPC472983
0.7471	Intermediate Similarity	NPC158411
0.7471	Intermediate Similarity	NPC38796
0.7471	Intermediate Similarity	NPC50964
0.747	Intermediate Similarity	NPC32832
0.747	Intermediate Similarity	NPC476795

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 NPC224455 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	141
0.1-0.2	1148
0.2-0.3	3675
0.3-0.4	2733
0.4-0.5	973
0.5-0.6	296
0.6-0.7	176
0.7-0.8	8
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
0.7609	Intermediate Similarity	NPD5778	Approved
0.7609	Intermediate Similarity	NPD5779	Approved
0.732	Intermediate Similarity	NPD7640	Approved
0.732	Intermediate Similarity	NPD7639	Approved
0.7312	Intermediate Similarity	NPD7637	Suspended
0.7262	Intermediate Similarity	NPD8264	Approved
0.7216	Intermediate Similarity	NPD7638	Approved
0.7204	Intermediate Similarity	NPD7838	Discovery
0.7143	Intermediate Similarity	NPD6648	Approved
0.7128	Intermediate Similarity	NPD7515	Phase 2
0.7126	Intermediate Similarity	NPD6929	Approved
0.7071	Intermediate Similarity	NPD5344	Discontinued
0.7051	Intermediate Similarity	NPD4191	Approved
0.7051	Intermediate Similarity	NPD4192	Approved
0.7051	Intermediate Similarity	NPD4194	Approved
0.7051	Intermediate Similarity	NPD4193	Approved
0.7045	Intermediate Similarity	NPD6930	Phase 2
0.7045	Intermediate Similarity	NPD7514	Phase 3
0.7045	Intermediate Similarity	NPD7332	Phase 2
0.7045	Intermediate Similarity	NPD6931	Approved
0.7041	Intermediate Similarity	NPD4225	Approved
0.7041	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD7145	Approved
0.7	Intermediate Similarity	NPD6695	Phase 3
0.6966	Remote Similarity	NPD6902	Approved
0.6957	Remote Similarity	NPD5279	Phase 3
0.6947	Remote Similarity	NPD5281	Approved
0.6947	Remote Similarity	NPD5284	Approved
0.6932	Remote Similarity	NPD4195	Approved
0.6923	Remote Similarity	NPD3665	Phase 1
0.6923	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD3666	Approved
0.6923	Remote Similarity	NPD3133	Approved
0.6915	Remote Similarity	NPD6101	Approved
0.6915	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD6925	Approved
0.6897	Remote Similarity	NPD5776	Phase 2
0.6889	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD5363	Approved
0.6835	Remote Similarity	NPD368	Approved
0.6818	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD7748	Approved
0.6782	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD3618	Phase 1
0.6774	Remote Similarity	NPD4623	Approved
0.6774	Remote Similarity	NPD4519	Discontinued
0.6771	Remote Similarity	NPD6411	Approved
0.6771	Remote Similarity	NPD6079	Approved
0.6744	Remote Similarity	NPD6926	Approved
0.6744	Remote Similarity	NPD6924	Approved
0.6739	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD342	Phase 1
0.6705	Remote Similarity	NPD6932	Approved
0.6703	Remote Similarity	NPD3667	Approved
0.6702	Remote Similarity	NPD7524	Approved
0.6702	Remote Similarity	NPD7750	Discontinued
0.6696	Remote Similarity	NPD7503	Approved
0.6667	Remote Similarity	NPD4821	Approved
0.6667	Remote Similarity	NPD4695	Discontinued
0.6667	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5211	Phase 2
0.6667	Remote Similarity	NPD6942	Approved
0.6667	Remote Similarity	NPD7339	Approved
0.6667	Remote Similarity	NPD4822	Approved
0.6667	Remote Similarity	NPD1696	Phase 3
0.6667	Remote Similarity	NPD6686	Approved
0.6667	Remote Similarity	NPD5221	Approved
0.6667	Remote Similarity	NPD6893	Approved
0.6667	Remote Similarity	NPD1694	Approved
0.6667	Remote Similarity	NPD7632	Discontinued
0.6667	Remote Similarity	NPD4819	Approved
0.6667	Remote Similarity	NPD4820	Approved
0.6667	Remote Similarity	NPD5222	Approved
0.6634	Remote Similarity	NPD6404	Discontinued
0.663	Remote Similarity	NPD5331	Approved
0.663	Remote Similarity	NPD5332	Approved
0.663	Remote Similarity	NPD5362	Discontinued
0.6629	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD4268	Approved
0.6629	Remote Similarity	NPD4271	Approved
0.66	Remote Similarity	NPD7902	Approved
0.66	Remote Similarity	NPD6083	Phase 2
0.66	Remote Similarity	NPD5173	Approved
0.66	Remote Similarity	NPD6084	Phase 2
0.6598	Remote Similarity	NPD7983	Approved
0.6596	Remote Similarity	NPD7334	Approved
0.6596	Remote Similarity	NPD7521	Approved
0.6596	Remote Similarity	NPD5330	Approved
0.6596	Remote Similarity	NPD6409	Approved
0.6596	Remote Similarity	NPD7146	Approved
0.6596	Remote Similarity	NPD6684	Approved
0.6593	Remote Similarity	NPD6898	Phase 1
0.6593	Remote Similarity	NPD4790	Discontinued
0.6591	Remote Similarity	NPD6933	Approved
0.6588	Remote Similarity	NPD7143	Approved
0.6588	Remote Similarity	NPD7144	Approved
0.6571	Remote Similarity	NPD5697	Approved
0.6566	Remote Similarity	NPD4629	Approved
0.6566	Remote Similarity	NPD5695	Phase 3
0.6566	Remote Similarity	NPD5210	Approved
0.6562	Remote Similarity	NPD4753	Phase 2
0.6562	Remote Similarity	NPD5328	Approved
0.6562	Remote Similarity	NPD6051	Approved
0.6559	Remote Similarity	NPD4786	Approved
0.6556	Remote Similarity	NPD7645	Phase 2
0.6538	Remote Similarity	NPD5141	Approved
0.6531	Remote Similarity	NPD6399	Phase 3
0.6522	Remote Similarity	NPD4269	Approved
0.6522	Remote Similarity	NPD4270	Approved
0.6517	Remote Similarity	NPD4756	Discovery
0.6514	Remote Similarity	NPD4632	Approved
0.6512	Remote Similarity	NPD7150	Approved
0.6512	Remote Similarity	NPD7151	Approved
0.6512	Remote Similarity	NPD7152	Approved
0.6509	Remote Similarity	NPD6011	Approved
0.6509	Remote Similarity	NPD6881	Approved
0.6509	Remote Similarity	NPD6899	Approved
0.65	Remote Similarity	NPD7839	Suspended
0.65	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6495	Remote Similarity	NPD46	Approved
0.6495	Remote Similarity	NPD5785	Approved
0.6495	Remote Similarity	NPD6698	Approved
0.6486	Remote Similarity	NPD7115	Discovery
0.6484	Remote Similarity	NPD7525	Registered
0.6484	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD5285	Approved
0.6471	Remote Similarity	NPD5286	Approved
0.6471	Remote Similarity	NPD4696	Approved
0.6471	Remote Similarity	NPD6923	Approved
0.6471	Remote Similarity	NPD6922	Approved
0.6458	Remote Similarity	NPD6672	Approved
0.6458	Remote Similarity	NPD6903	Approved
0.6458	Remote Similarity	NPD5737	Approved
0.6458	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD7154	Phase 3
0.6449	Remote Similarity	NPD6014	Approved
0.6449	Remote Similarity	NPD6013	Approved
0.6449	Remote Similarity	NPD6012	Approved
0.6442	Remote Similarity	NPD6647	Phase 2
0.6437	Remote Similarity	NPD4732	Discontinued
0.6429	Remote Similarity	NPD5694	Approved
0.6429	Remote Similarity	NPD7087	Discontinued
0.6429	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD6053	Discontinued
0.6421	Remote Similarity	NPD4694	Approved
0.6421	Remote Similarity	NPD5690	Phase 2
0.6421	Remote Similarity	NPD4249	Approved
0.6421	Remote Similarity	NPD5280	Approved
0.641	Remote Similarity	NPD4219	Approved
0.6408	Remote Similarity	NPD5223	Approved
0.6389	Remote Similarity	NPD7290	Approved
0.6389	Remote Similarity	NPD6883	Approved
0.6389	Remote Similarity	NPD7102	Approved
0.6386	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD6683	Phase 2
0.6373	Remote Similarity	NPD5696	Approved
0.6373	Remote Similarity	NPD5290	Discontinued
0.6364	Remote Similarity	NPD4202	Approved
0.6354	Remote Similarity	NPD3573	Approved
0.6354	Remote Similarity	NPD4251	Approved
0.6354	Remote Similarity	NPD4250	Approved
0.6346	Remote Similarity	NPD4633	Approved
0.6346	Remote Similarity	NPD5224	Approved
0.6346	Remote Similarity	NPD5225	Approved
0.6346	Remote Similarity	NPD5226	Approved
0.6344	Remote Similarity	NPD4221	Approved
0.6344	Remote Similarity	NPD4223	Phase 3
0.6344	Remote Similarity	NPD5209	Approved
0.6339	Remote Similarity	NPD6009	Approved
0.6337	Remote Similarity	NPD4697	Phase 3
0.633	Remote Similarity	NPD8130	Phase 1
0.633	Remote Similarity	NPD6649	Approved
0.633	Remote Similarity	NPD6847	Approved
0.633	Remote Similarity	NPD6869	Approved
0.633	Remote Similarity	NPD6617	Approved
0.633	Remote Similarity	NPD6650	Approved
0.6327	Remote Similarity	NPD7136	Phase 2
0.6327	Remote Similarity	NPD5692	Phase 3
0.6327	Remote Similarity	NPD5207	Approved
0.6321	Remote Similarity	NPD5739	Approved
0.6321	Remote Similarity	NPD6675	Approved
0.6321	Remote Similarity	NPD7128	Approved
0.6321	Remote Similarity	NPD6402	Approved
0.6304	Remote Similarity	NPD4252	Approved
0.6304	Remote Similarity	NPD7509	Discontinued
0.63	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.63	Remote Similarity	NPD7900	Approved
0.6296	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6292	Remote Similarity	NPD8039	Approved
0.6286	Remote Similarity	NPD5175	Approved
0.6286	Remote Similarity	NPD5174	Approved
0.6277	Remote Similarity	NPD6110	Phase 1
0.6275	Remote Similarity	NPD4755	Approved
0.6273	Remote Similarity	NPD8297	Approved
0.6273	Remote Similarity	NPD6882	Approved
0.6265	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6263	Remote Similarity	NPD6050	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