NPASS Compound

Structure

NPC469819 OpenBabel07101719512D 33 34 0 0 1 0 0 0 0 0999 V2000 -0.8660 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5388 -3.9641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0388 -4.8301 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2202 2.7406 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3621 3.4451 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 -2.2321 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4049 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5388 -2.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0388 -3.0981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1810 1.7226 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0388 -1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4067 0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5388 -3.9641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2257 2.6361 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 1.5388 -0.5000 0.0000 C 0 0 2 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 -2.5000 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 0.0000 -1.0000 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 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5388 -0.5000 0.0000 C 0 0 2 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 -1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5388 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -1.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 10 1 0 0 0 0 2 17 1 0 0 0 0 3 17 1 0 0 0 0 4 18 1 0 0 0 0 5 18 1 0 0 0 0 6 19 1 0 0 0 0 7 26 1 0 0 0 0 8 26 1 0 0 0 0 10 19 1 0 0 0 0 11 12 1 0 0 0 0 11 14 1 0 0 0 0 12 17 2 0 0 0 0 13 15 1 0 0 0 0 13 18 2 0 0 0 0 14 27 1 0 0 0 0 16 20 1 0 0 0 0 16 28 1 0 0 0 0 19 22 1 0 0 0 0 20 27 1 6 0 0 0 20 33 1 0 0 0 0 21 22 1 0 0 0 0 21 23 1 0 0 0 0 21 24 2 0 0 0 0 22 29 2 0 0 0 0 23 26 1 0 0 0 0 23 30 2 0 0 0 0 24 28 1 0 0 0 0 24 33 1 0 0 0 0 25 26 1 0 0 0 0 25 28 1 0 0 0 0 25 31 2 0 0 0 0 27 9 1 6 0 0 0 27 32 1 0 0 0 0 28 15 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	458.3
Volume:	503.864
LogP:	6.107
LogD:	4.475
LogS:	-5.149
# Rotatable Bonds:	9
TPSA:	80.67
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.274
Synthetic Accessibility Score:	4.83
Fsp3:	0.679
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.757
MDCK Permeability:	1.7205327822011895e-05
Pgp-inhibitor:	0.878
Pgp-substrate:	0.981
Human Intestinal Absorption (HIA):	0.022
20% Bioavailability (F20%):	0.802
30% Bioavailability (F30%):	0.888

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.045
Plasma Protein Binding (PPB):	89.44768524169922%
Volume Distribution (VD):	2.364
Pgp-substrate:	6.4827775955200195%

ADMET: Metabolism

CYP1A2-inhibitor:	0.049
CYP1A2-substrate:	0.566
CYP2C19-inhibitor:	0.759
CYP2C19-substrate:	0.82
CYP2C9-inhibitor:	0.502
CYP2C9-substrate:	0.065
CYP2D6-inhibitor:	0.55
CYP2D6-substrate:	0.012
CYP3A4-inhibitor:	0.864
CYP3A4-substrate:	0.907

ADMET: Excretion

Clearance (CL):	7.863
Half-life (T1/2):	0.053

ADMET: Toxicity

hERG Blockers:	0.002
Human Hepatotoxicity (H-HT):	0.954
Drug-inuced Liver Injury (DILI):	0.93
AMES Toxicity:	0.078
Rat Oral Acute Toxicity:	0.283
Maximum Recommended Daily Dose:	0.088
Skin Sensitization:	0.262
Carcinogencity:	0.508
Eye Corrosion:	0.003
Eye Irritation:	0.014
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: NPC469819

Natural Product ID:	NPC469819
*Common Name:**	Petiolin L
IUPAC Name:	(2R,3aS)-2-[(2S)-2-hydroxy-6-methylhept-5-en-2-yl]-5,5-dimethyl-7-(2-methylbutanoyl)-3a-(3-methylbut-2-enyl)-2,3-dihydro-1-benzofuran-4,6-dione
Synonyms:	Petiolin L
Standard InCHIKey:	MIHKHHYYLFLYDS-VJHUIPRKSA-N
Standard InCHI:	InChI=1S/C28H42O5/c1-10-19(6)22(29)21-23(30)26(7,8)25(31)28(15-13-18(4)5)16-20(33-24(21)28)27(9,32)14-11-12-17(2)3/h12-13,19-20,32H,10-11,14-16H2,1-9H3/t19?,20-,27+,28+/m1/s1
SMILES:	CCC(C(=O)C1=C2O[C@H](C[C@]2(CC=C(C)C)C(=O)C(C1=O)(C)C)[C@](CCC=C(C)C)(O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1209769
PubChem CID:	49862717
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000301] Benzofurans

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO12794.1	Hypericum pseudopetiolatum	Under-species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[18430575]
NPO12794.1	Hypericum pseudopetiolatum	Under-species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[20598881]

☑ 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
MIC	1

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT137	Cell Line	L1210	Mus musculus	IC50	>	10.0	ug.mL-1	PMID[558113]
NPT91	Cell Line	KB	Homo sapiens	MIC	>	10.0	ug.mL-1	PMID[558113]

☑ 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 NPC469819 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	190
0.1-0.2	1272
0.2-0.3	5353
0.3-0.4	10005
0.4-0.5	13868
0.5-0.6	7658
0.6-0.7	3983
0.7-0.8	323
0.8-0.85	29
0.85-0.9	11
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC114162
0.9239	High Similarity	NPC27105
0.914	High Similarity	NPC471330
0.914	High Similarity	NPC471331
0.914	High Similarity	NPC203388
0.914	High Similarity	NPC472687
0.914	High Similarity	NPC99657
0.913	High Similarity	NPC93271
0.913	High Similarity	NPC135576
0.8936	High Similarity	NPC153776
0.8936	High Similarity	NPC177680
0.8936	High Similarity	NPC472730
0.8936	High Similarity	NPC472729
0.8842	High Similarity	NPC472728
0.8842	High Similarity	NPC472727
0.8723	High Similarity	NPC472733
0.8723	High Similarity	NPC472734
0.8632	High Similarity	NPC472731
0.8632	High Similarity	NPC472732
0.8632	High Similarity	NPC239895
0.8586	High Similarity	NPC471333
0.8586	High Similarity	NPC471332
0.8526	High Similarity	NPC21681
0.8526	High Similarity	NPC472675
0.8316	Intermediate Similarity	NPC477241
0.8295	Intermediate Similarity	NPC472948
0.8182	Intermediate Similarity	NPC9878
0.8065	Intermediate Similarity	NPC38885
0.8021	Intermediate Similarity	NPC61275
0.8	Intermediate Similarity	NPC476134
0.8	Intermediate Similarity	NPC101067
0.7979	Intermediate Similarity	NPC476707
0.7979	Intermediate Similarity	NPC228415
0.7979	Intermediate Similarity	NPC476706
0.7979	Intermediate Similarity	NPC476708
0.7979	Intermediate Similarity	NPC87189
0.7917	Intermediate Similarity	NPC146852
0.7843	Intermediate Similarity	NPC475321
0.7822	Intermediate Similarity	NPC181645
0.7778	Intermediate Similarity	NPC247069
0.7778	Intermediate Similarity	NPC8803
0.7767	Intermediate Similarity	NPC472756
0.7732	Intermediate Similarity	NPC476705
0.77	Intermediate Similarity	NPC472689
0.77	Intermediate Similarity	NPC472690
0.77	Intermediate Similarity	NPC477268
0.77	Intermediate Similarity	NPC477267
0.7647	Intermediate Similarity	NPC477871
0.7647	Intermediate Similarity	NPC477870
0.7647	Intermediate Similarity	NPC476213
0.7647	Intermediate Similarity	NPC472753
0.7647	Intermediate Similarity	NPC476246
0.7647	Intermediate Similarity	NPC471401
0.7642	Intermediate Similarity	NPC470257
0.7629	Intermediate Similarity	NPC469464
0.7609	Intermediate Similarity	NPC189237
0.7604	Intermediate Similarity	NPC143025
0.7604	Intermediate Similarity	NPC269677
0.7604	Intermediate Similarity	NPC476704
0.7596	Intermediate Similarity	NPC255309
0.7573	Intermediate Similarity	NPC476235
0.7573	Intermediate Similarity	NPC476126
0.7573	Intermediate Similarity	NPC472754
0.7573	Intermediate Similarity	NPC70369
0.7549	Intermediate Similarity	NPC54705
0.7549	Intermediate Similarity	NPC46761
0.7527	Intermediate Similarity	NPC477269
0.7527	Intermediate Similarity	NPC477271
0.7527	Intermediate Similarity	NPC477270
0.7527	Intermediate Similarity	NPC129080
0.7526	Intermediate Similarity	NPC307411
0.7525	Intermediate Similarity	NPC20078
0.7525	Intermediate Similarity	NPC473574
0.7525	Intermediate Similarity	NPC124246
0.7525	Intermediate Similarity	NPC273269
0.7524	Intermediate Similarity	NPC292588
0.7524	Intermediate Similarity	NPC96377
0.75	Intermediate Similarity	NPC475873
0.75	Intermediate Similarity	NPC472755
0.7477	Intermediate Similarity	NPC153239
0.7473	Intermediate Similarity	NPC478247
0.7473	Intermediate Similarity	NPC478246
0.7453	Intermediate Similarity	NPC43285
0.7453	Intermediate Similarity	NPC58370
0.7449	Intermediate Similarity	NPC166554
0.7449	Intermediate Similarity	NPC51004
0.7431	Intermediate Similarity	NPC205534
0.7429	Intermediate Similarity	NPC470104
0.7429	Intermediate Similarity	NPC13385
0.7426	Intermediate Similarity	NPC473164
0.7423	Intermediate Similarity	NPC474854
0.7423	Intermediate Similarity	NPC472008
0.7419	Intermediate Similarity	NPC44963
0.7419	Intermediate Similarity	NPC472684
0.7411	Intermediate Similarity	NPC106644
0.7404	Intermediate Similarity	NPC225353
0.7404	Intermediate Similarity	NPC183571
0.7404	Intermediate Similarity	NPC163249
0.74	Intermediate Similarity	NPC14322
0.7383	Intermediate Similarity	NPC19412
0.7383	Intermediate Similarity	NPC473288
0.7374	Intermediate Similarity	NPC30515
0.7374	Intermediate Similarity	NPC184463
0.7374	Intermediate Similarity	NPC475441
0.7364	Intermediate Similarity	NPC326264
0.7358	Intermediate Similarity	NPC253223
0.7358	Intermediate Similarity	NPC102352
0.7353	Intermediate Similarity	NPC17326
0.7353	Intermediate Similarity	NPC473161
0.7353	Intermediate Similarity	NPC134454
0.7339	Intermediate Similarity	NPC474229
0.7339	Intermediate Similarity	NPC324683
0.7333	Intermediate Similarity	NPC474165
0.7333	Intermediate Similarity	NPC114236
0.7333	Intermediate Similarity	NPC110989
0.7333	Intermediate Similarity	NPC69171
0.7333	Intermediate Similarity	NPC320294
0.7333	Intermediate Similarity	NPC472747
0.7333	Intermediate Similarity	NPC472750
0.7327	Intermediate Similarity	NPC108141
0.7327	Intermediate Similarity	NPC31021
0.732	Intermediate Similarity	NPC472007
0.732	Intermediate Similarity	NPC179659
0.732	Intermediate Similarity	NPC23622
0.7315	Intermediate Similarity	NPC250018
0.7312	Intermediate Similarity	NPC279667
0.7312	Intermediate Similarity	NPC103634
0.7308	Intermediate Similarity	NPC47880
0.7308	Intermediate Similarity	NPC474742
0.7308	Intermediate Similarity	NPC476270
0.73	Intermediate Similarity	NPC477615
0.73	Intermediate Similarity	NPC476300
0.7297	Intermediate Similarity	NPC473898
0.7292	Intermediate Similarity	NPC79573
0.7292	Intermediate Similarity	NPC475206
0.729	Intermediate Similarity	NPC3316
0.729	Intermediate Similarity	NPC144854
0.7282	Intermediate Similarity	NPC147954
0.7282	Intermediate Similarity	NPC300584
0.7281	Intermediate Similarity	NPC478051
0.7273	Intermediate Similarity	NPC476004
0.7273	Intermediate Similarity	NPC474761
0.7273	Intermediate Similarity	NPC472325
0.7273	Intermediate Similarity	NPC158388
0.7273	Intermediate Similarity	NPC207251
0.7273	Intermediate Similarity	NPC478004
0.7273	Intermediate Similarity	NPC269530
0.7273	Intermediate Similarity	NPC478003
0.7273	Intermediate Similarity	NPC265856
0.7264	Intermediate Similarity	NPC471293
0.7264	Intermediate Similarity	NPC40170
0.7264	Intermediate Similarity	NPC472748
0.7264	Intermediate Similarity	NPC146731
0.7264	Intermediate Similarity	NPC203659
0.7263	Intermediate Similarity	NPC62214
0.7257	Intermediate Similarity	NPC17772
0.7255	Intermediate Similarity	NPC21302
0.7255	Intermediate Similarity	NPC11396
0.7248	Intermediate Similarity	NPC99760
0.7248	Intermediate Similarity	NPC474567
0.7248	Intermediate Similarity	NPC286880
0.7245	Intermediate Similarity	NPC58532
0.7245	Intermediate Similarity	NPC472677
0.7245	Intermediate Similarity	NPC202672
0.7241	Intermediate Similarity	NPC265557
0.7241	Intermediate Similarity	NPC18945
0.7241	Intermediate Similarity	NPC105926
0.7241	Intermediate Similarity	NPC91693
0.7238	Intermediate Similarity	NPC473163
0.7238	Intermediate Similarity	NPC283567
0.7238	Intermediate Similarity	NPC474747
0.7238	Intermediate Similarity	NPC149371
0.7232	Intermediate Similarity	NPC207217
0.7232	Intermediate Similarity	NPC173686
0.7232	Intermediate Similarity	NPC16081
0.7228	Intermediate Similarity	NPC196227
0.7228	Intermediate Similarity	NPC473172
0.7228	Intermediate Similarity	NPC318332
0.7222	Intermediate Similarity	NPC469508
0.7222	Intermediate Similarity	NPC277017
0.7222	Intermediate Similarity	NPC154608
0.7222	Intermediate Similarity	NPC192813
0.7217	Intermediate Similarity	NPC471999
0.7217	Intermediate Similarity	NPC472000
0.7216	Intermediate Similarity	NPC477478
0.7216	Intermediate Similarity	NPC477479
0.7216	Intermediate Similarity	NPC203795
0.7216	Intermediate Similarity	NPC472009
0.7216	Intermediate Similarity	NPC470345
0.7212	Intermediate Similarity	NPC474720
0.7207	Intermediate Similarity	NPC198539
0.72	Intermediate Similarity	NPC12172
0.72	Intermediate Similarity	NPC230623
0.72	Intermediate Similarity	NPC208886
0.72	Intermediate Similarity	NPC116726
0.7196	Intermediate Similarity	NPC32006
0.7196	Intermediate Similarity	NPC472751
0.7196	Intermediate Similarity	NPC190867
0.7196	Intermediate Similarity	NPC472749
0.7196	Intermediate Similarity	NPC181357

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 NPC469819 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	168
0.1-0.2	1901
0.2-0.3	4045
0.3-0.4	2082
0.4-0.5	572
0.5-0.6	234
0.6-0.7	147
0.7-0.8	1
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
0.7755	Intermediate Similarity	NPD5282	Discontinued
0.7011	Intermediate Similarity	NPD7331	Phase 2
0.6979	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD6110	Phase 1
0.6897	Remote Similarity	NPD7341	Phase 2
0.6838	Remote Similarity	NPD6054	Approved
0.6838	Remote Similarity	NPD6059	Approved
0.6832	Remote Similarity	NPD5328	Approved
0.6827	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD6412	Phase 2
0.6792	Remote Similarity	NPD5696	Approved
0.6786	Remote Similarity	NPD4634	Approved
0.6786	Remote Similarity	NPD6371	Approved
0.6723	Remote Similarity	NPD6370	Approved
0.67	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.67	Remote Similarity	NPD3618	Phase 1
0.6699	Remote Similarity	NPD6411	Approved
0.6699	Remote Similarity	NPD7983	Approved
0.6699	Remote Similarity	NPD6079	Approved
0.6695	Remote Similarity	NPD6319	Approved
0.6667	Remote Similarity	NPD5210	Approved
0.6667	Remote Similarity	NPD3133	Approved
0.6667	Remote Similarity	NPD4629	Approved
0.6667	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3665	Phase 1
0.6667	Remote Similarity	NPD3666	Approved
0.6639	Remote Similarity	NPD6015	Approved
0.6639	Remote Similarity	NPD6016	Approved
0.6636	Remote Similarity	NPD4225	Approved
0.6635	Remote Similarity	NPD5778	Approved
0.6635	Remote Similarity	NPD6399	Phase 3
0.6635	Remote Similarity	NPD5779	Approved
0.6612	Remote Similarity	NPD7492	Approved
0.6609	Remote Similarity	NPD4632	Approved
0.6604	Remote Similarity	NPD4697	Phase 3
0.6602	Remote Similarity	NPD46	Approved
0.6602	Remote Similarity	NPD6698	Approved
0.6598	Remote Similarity	NPD4695	Discontinued
0.6583	Remote Similarity	NPD5988	Approved
0.6581	Remote Similarity	NPD7115	Discovery
0.6577	Remote Similarity	NPD5739	Approved
0.6577	Remote Similarity	NPD7128	Approved
0.6577	Remote Similarity	NPD6675	Approved
0.6577	Remote Similarity	NPD6402	Approved
0.6577	Remote Similarity	NPD6008	Approved
0.6571	Remote Similarity	NPD7748	Approved
0.6557	Remote Similarity	NPD6616	Approved
0.6549	Remote Similarity	NPD6373	Approved
0.6549	Remote Similarity	NPD6372	Approved
0.6542	Remote Similarity	NPD6083	Phase 2
0.6542	Remote Similarity	NPD7902	Approved
0.6542	Remote Similarity	NPD4755	Approved
0.6542	Remote Similarity	NPD6084	Phase 2
0.6535	Remote Similarity	NPD7521	Approved
0.6535	Remote Similarity	NPD5330	Approved
0.6535	Remote Similarity	NPD6684	Approved
0.6535	Remote Similarity	NPD7334	Approved
0.6535	Remote Similarity	NPD6409	Approved
0.6535	Remote Similarity	NPD7146	Approved
0.6535	Remote Similarity	NPD5279	Phase 3
0.6531	Remote Similarity	NPD5369	Approved
0.6529	Remote Similarity	NPD8328	Phase 3
0.6522	Remote Similarity	NPD8297	Approved
0.6509	Remote Similarity	NPD5695	Phase 3
0.6505	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD6101	Approved
0.6505	Remote Similarity	NPD4753	Phase 2
0.6504	Remote Similarity	NPD8293	Discontinued
0.6504	Remote Similarity	NPD7078	Approved
0.65	Remote Similarity	NPD4786	Approved
0.6465	Remote Similarity	NPD4223	Phase 3
0.6465	Remote Similarity	NPD4221	Approved
0.6465	Remote Similarity	NPD3667	Approved
0.646	Remote Similarity	NPD6881	Approved
0.646	Remote Similarity	NPD7320	Approved
0.646	Remote Similarity	NPD6686	Approved
0.646	Remote Similarity	NPD6899	Approved
0.6452	Remote Similarity	NPD6033	Approved
0.6452	Remote Similarity	NPD7736	Approved
0.6449	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6449	Remote Similarity	NPD5221	Approved
0.6449	Remote Similarity	NPD5222	Approved
0.6442	Remote Similarity	NPD5785	Approved
0.6436	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD5329	Approved
0.6435	Remote Similarity	NPD6650	Approved
0.6435	Remote Similarity	NPD6649	Approved
0.6422	Remote Similarity	NPD5286	Approved
0.6422	Remote Similarity	NPD5285	Approved
0.6422	Remote Similarity	NPD4700	Approved
0.6422	Remote Similarity	NPD4696	Approved
0.6408	Remote Similarity	NPD5737	Approved
0.6408	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD6672	Approved
0.6408	Remote Similarity	NPD6903	Approved
0.6389	Remote Similarity	NPD5173	Approved
0.6381	Remote Similarity	NPD7515	Phase 2
0.6379	Remote Similarity	NPD6053	Discontinued
0.6373	Remote Similarity	NPD5786	Approved
0.6372	Remote Similarity	NPD5697	Approved
0.6372	Remote Similarity	NPD5701	Approved
0.6364	Remote Similarity	NPD5223	Approved
0.6355	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6348	Remote Similarity	NPD7102	Approved
0.6348	Remote Similarity	NPD7290	Approved
0.6348	Remote Similarity	NPD6883	Approved
0.6337	Remote Similarity	NPD4197	Approved
0.6321	Remote Similarity	NPD4202	Approved
0.6316	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD6011	Approved
0.6306	Remote Similarity	NPD5225	Approved
0.6306	Remote Similarity	NPD4633	Approved
0.6306	Remote Similarity	NPD5226	Approved
0.6306	Remote Similarity	NPD5224	Approved
0.6306	Remote Similarity	NPD5211	Phase 2
0.6303	Remote Similarity	NPD6009	Approved
0.63	Remote Similarity	NPD6435	Approved
0.6299	Remote Similarity	NPD7260	Phase 2
0.6293	Remote Similarity	NPD6847	Approved
0.6293	Remote Similarity	NPD6869	Approved
0.6293	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6293	Remote Similarity	NPD6617	Approved
0.6293	Remote Similarity	NPD8130	Phase 1
0.6275	Remote Similarity	NPD5363	Approved
0.6275	Remote Similarity	NPD1694	Approved
0.6262	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD7900	Approved
0.6261	Remote Similarity	NPD6013	Approved
0.6261	Remote Similarity	NPD6012	Approved
0.6261	Remote Similarity	NPD6014	Approved
0.626	Remote Similarity	NPD7604	Phase 2
0.625	Remote Similarity	NPD5175	Approved
0.625	Remote Similarity	NPD5174	Approved
0.625	Remote Similarity	NPD4754	Approved
0.6239	Remote Similarity	NPD6882	Approved
0.6238	Remote Similarity	NPD7154	Phase 3
0.623	Remote Similarity	NPD5983	Phase 2
0.6226	Remote Similarity	NPD5284	Approved
0.6226	Remote Similarity	NPD5281	Approved
0.6224	Remote Similarity	NPD3617	Approved
0.6214	Remote Similarity	NPD4688	Approved
0.6214	Remote Similarity	NPD4623	Approved
0.6214	Remote Similarity	NPD5690	Phase 2
0.6214	Remote Similarity	NPD4689	Approved
0.6214	Remote Similarity	NPD4138	Approved
0.6214	Remote Similarity	NPD4694	Approved
0.6214	Remote Similarity	NPD5205	Approved
0.6214	Remote Similarity	NPD4693	Phase 3
0.6214	Remote Similarity	NPD5280	Approved
0.6214	Remote Similarity	NPD4519	Discontinued
0.6214	Remote Similarity	NPD4690	Approved
0.6195	Remote Similarity	NPD5141	Approved
0.619	Remote Similarity	NPD6673	Approved
0.619	Remote Similarity	NPD6904	Approved
0.619	Remote Similarity	NPD6080	Approved
0.6182	Remote Similarity	NPD7638	Approved
0.6176	Remote Similarity	NPD3668	Phase 3
0.616	Remote Similarity	NPD6336	Discontinued
0.6154	Remote Similarity	NPD3573	Approved
0.6154	Remote Similarity	NPD7524	Approved
0.6147	Remote Similarity	NPD7839	Suspended
0.6142	Remote Similarity	NPD7319	Approved
0.614	Remote Similarity	NPD4767	Approved
0.614	Remote Similarity	NPD4768	Approved
0.6139	Remote Similarity	NPD4270	Approved
0.6139	Remote Similarity	NPD4269	Approved
0.6139	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6132	Remote Similarity	NPD5207	Approved
0.6126	Remote Similarity	NPD7640	Approved
0.6126	Remote Similarity	NPD7639	Approved
0.6124	Remote Similarity	NPD6845	Suspended
0.6121	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.61	Remote Similarity	NPD5368	Approved
0.61	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6098	Remote Similarity	NPD8517	Approved
0.6098	Remote Similarity	NPD8513	Phase 3
0.6098	Remote Similarity	NPD8515	Approved
0.6098	Remote Similarity	NPD8516	Approved
0.6087	Remote Similarity	NPD3704	Approved
0.6078	Remote Similarity	NPD4788	Approved
0.6075	Remote Similarity	NPD6050	Approved
0.6068	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6066	Remote Similarity	NPD4522	Approved
0.6061	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6048	Remote Similarity	NPD8080	Discontinued
0.6038	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6034	Remote Similarity	NPD4729	Approved
0.6034	Remote Similarity	NPD5128	Approved
0.6034	Remote Similarity	NPD4730	Approved
0.6033	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6032	Remote Similarity	NPD7507	Approved
0.6018	Remote Similarity	NPD5091	Approved
0.6017	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6067	Discontinued
0.6	Remote Similarity	NPD7614	Phase 1
0.5984	Remote Similarity	NPD6335	Approved
0.5983	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.5981	Remote Similarity	NPD4096	Approved
0.5981	Remote Similarity	NPD7838	Discovery
0.5981	Remote Similarity	NPD5692	Phase 3

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