NPASS Compound

Structure

CID56656 OpenBabel06191715392D 28 32 0 0 1 0 0 0 0 0999 V2000 2.8619 -1.9222 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1957 2.4811 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1591 0.4142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8810 -1.6364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7802 -3.1527 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0001 -2.7023 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9175 -0.9126 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2924 -2.0592 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5602 -1.8015 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0002 0.1771 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7801 -0.4504 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0106 -1.9222 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4109 1.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5602 -2.7023 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -1.8015 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6606 -0.5583 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6809 -1.3511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0338 -0.1575 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.3743 -0.4328 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7800 -1.3511 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7801 -1.3511 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7801 -0.4504 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.2521 1.3969 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1065 -0.6138 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0316 0.7140 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6494 -0.3607 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7850 1.0241 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 12 2 0 0 0 0 2 13 1 0 0 0 0 4 7 1 0 0 0 0 4 8 1 0 0 0 0 5 6 1 0 0 0 0 6 15 1 0 0 0 0 7 19 1 0 0 0 0 9 14 1 0 0 0 0 9 21 1 0 0 0 0 10 19 1 0 0 0 0 10 27 1 0 0 0 0 11 20 1 0 0 0 0 11 28 1 0 0 0 0 12 14 1 0 0 0 0 12 17 1 0 0 0 0 13 23 2 0 0 0 0 13 27 1 0 0 0 0 14 5 1 6 0 0 0 15 20 1 1 0 0 0 15 21 1 0 0 0 0 16 18 1 0 0 0 0 16 19 1 1 0 0 0 16 20 1 0 0 0 0 17 21 1 0 0 0 0 17 24 2 0 0 0 0 18 22 1 6 0 0 0 18 25 1 0 0 0 0 19 3 1 6 0 0 0 20 8 1 6 0 0 0 21 22 1 1 0 0 0 22 26 1 1 0 0 0 22 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	390.2
Volume:	391.118
LogP:	1.689
LogD:	1.778
LogS:	-3.881
# Rotatable Bonds:	3
TPSA:	93.06
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	6
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.553
Synthetic Accessibility Score:	6.75
Fsp3:	0.818
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.237
MDCK Permeability:	4.0076520235743374e-05
Pgp-inhibitor:	0.074
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.013
20% Bioavailability (F20%):	0.217
30% Bioavailability (F30%):	0.954

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.652
Plasma Protein Binding (PPB):	70.9858627319336%
Volume Distribution (VD):	1.489
Pgp-substrate:	36.79841613769531%

ADMET: Metabolism

CYP1A2-inhibitor:	0.024
CYP1A2-substrate:	0.328
CYP2C19-inhibitor:	0.052
CYP2C19-substrate:	0.643
CYP2C9-inhibitor:	0.09
CYP2C9-substrate:	0.028
CYP2D6-inhibitor:	0.012
CYP2D6-substrate:	0.132
CYP3A4-inhibitor:	0.72
CYP3A4-substrate:	0.226

ADMET: Excretion

Clearance (CL):	2.023
Half-life (T1/2):	0.762

ADMET: Toxicity

hERG Blockers:	0.11
Human Hepatotoxicity (H-HT):	0.205
Drug-inuced Liver Injury (DILI):	0.161
AMES Toxicity:	0.378
Rat Oral Acute Toxicity:	0.485
Maximum Recommended Daily Dose:	0.89
Skin Sensitization:	0.713
Carcinogencity:	0.312
Eye Corrosion:	0.004
Eye Irritation:	0.082
Respiratory Toxicity:	0.957

Download Data

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

Natural Product: NPC56656

Natural Product ID:	NPC56656
*Common Name:**	Longikaurin C
IUPAC Name:	n.a.
Synonyms:	Longikaurin C
Standard InCHIKey:	HSMCZGYOVWATPU-AQXMTESMSA-N
Standard InCHI:	InChI=1S/C22H30O6/c1-12-14-5-6-15-20-8-4-7-19(3,10-27-13(2)23)16(20)18(25)22(26,28-11-20)21(15,9-14)17(12)24/h14-16,18,25-26H,1,4-11H2,2-3H3/t14-,15+,16-,18+,19+,20-,21+,22+/m1/s1
SMILES:	C=C1[C@@H]2CC[C@H]3[C@@]45CCC[C@@](C)(COC(=O)C)[C@H]5[C@@H]([C@]([C@]3(C2)C1=O)(O)OC4)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL519320
PubChem CID:	44586034
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
NPO26266	Isodon japonicus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1039/C39730000707]
NPO1927	Isodon eriocalyx	Species	Lamiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[17020288]
NPO26266	Isodon japonicus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18491868]
NPO1927	Isodon eriocalyx	Species	Lamiaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[20949916]
NPO1927	Isodon eriocalyx	Species	Lamiaceae	Eukaryota	aerial parts	n.a.	n.a.	PMID[20949916]
NPO1927	Isodon eriocalyx	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22624550]
NPO13628	Rabdosia longituba	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13628	Rabdosia longituba	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1927	Isodon eriocalyx	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26266	Isodon japonicus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13628	Rabdosia longituba	Species	Lamiaceae	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	4

Activity Type	# Activity
Cell Line	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	1000.0	nM	PMID[523191]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	2100.0	nM	PMID[523192]
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	=	2900.0	nM	PMID[523192]
NPT146	Cell Line	SK-OV-3	Homo sapiens	IC50	=	3300.0	nM	PMID[523192]

☑ 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 NPC56656 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	277
0.1-0.2	1937
0.2-0.3	6063
0.3-0.4	11311
0.4-0.5	9666
0.5-0.6	5961
0.6-0.7	4405
0.7-0.8	2461
0.8-0.85	473
0.85-0.9	76
0.9-0.95	35
0.95-1	32

Similarity Score	Similarity Level	Natural Product ID
0.9898	High Similarity	NPC471474
0.9798	High Similarity	NPC471094
0.9798	High Similarity	NPC473410
0.9798	High Similarity	NPC469984
0.97	High Similarity	NPC102741
0.97	High Similarity	NPC131903
0.9697	High Similarity	NPC186054
0.9604	High Similarity	NPC320383
0.9604	High Similarity	NPC85391
0.9604	High Similarity	NPC474786
0.9604	High Similarity	NPC137104
0.96	High Similarity	NPC63841
0.9596	High Similarity	NPC130511
0.9596	High Similarity	NPC307660
0.951	High Similarity	NPC213320
0.9505	High Similarity	NPC274827
0.9417	High Similarity	NPC473397
0.9417	High Similarity	NPC474927
0.9417	High Similarity	NPC473352
0.9412	High Similarity	NPC471093
0.9406	High Similarity	NPC89860
0.9406	High Similarity	NPC189663
0.9327	High Similarity	NPC132668
0.932	High Similarity	NPC29505
0.9314	High Similarity	NPC252679
0.9314	High Similarity	NPC118721
0.9307	High Similarity	NPC67745
0.9307	High Similarity	NPC471461
0.9223	High Similarity	NPC471476
0.9216	High Similarity	NPC55973
0.92	High Similarity	NPC277074
0.92	High Similarity	NPC209298
0.92	High Similarity	NPC139347
0.9192	High Similarity	NPC14634
0.9151	High Similarity	NPC229752
0.9151	High Similarity	NPC88945
0.9143	High Similarity	NPC194273
0.9143	High Similarity	NPC320118
0.9143	High Similarity	NPC471252
0.9135	High Similarity	NPC63244
0.9109	High Similarity	NPC202793
0.9091	High Similarity	NPC470388
0.9065	High Similarity	NPC78836
0.9057	High Similarity	NPC243354
0.9048	High Similarity	NPC471244
0.9048	High Similarity	NPC157929
0.9048	High Similarity	NPC145625
0.9038	High Similarity	NPC473324
0.9029	High Similarity	NPC232133
0.901	High Similarity	NPC122811
0.8962	High Similarity	NPC94141
0.8962	High Similarity	NPC471248
0.8952	High Similarity	NPC56025
0.8952	High Similarity	NPC122339
0.8952	High Similarity	NPC471243
0.8942	High Similarity	NPC469983
0.8932	High Similarity	NPC166993
0.8889	High Similarity	NPC473304
0.8879	High Similarity	NPC17165
0.8868	High Similarity	NPC471245
0.8868	High Similarity	NPC473303
0.8846	High Similarity	NPC273155
0.8835	High Similarity	NPC138908
0.8835	High Similarity	NPC200957
0.8812	High Similarity	NPC252614
0.88	High Similarity	NPC471038
0.88	High Similarity	NPC474793
0.875	High Similarity	NPC469746
0.875	High Similarity	NPC88833
0.875	High Similarity	NPC96333
0.8738	High Similarity	NPC301787
0.8738	High Similarity	NPC474558
0.8725	High Similarity	NPC475803
0.8725	High Similarity	NPC309388
0.8713	High Similarity	NPC267921
0.8692	High Similarity	NPC205534
0.8687	High Similarity	NPC470232
0.8667	High Similarity	NPC218123
0.8667	High Similarity	NPC112895
0.8667	High Similarity	NPC231278
0.8654	High Similarity	NPC222833
0.8654	High Similarity	NPC164600
0.8654	High Similarity	NPC103172
0.8641	High Similarity	NPC96217
0.8627	High Similarity	NPC236585
0.8627	High Similarity	NPC148279
0.8627	High Similarity	NPC46848
0.8614	High Similarity	NPC26270
0.8611	High Similarity	NPC73986
0.86	High Similarity	NPC200054
0.86	High Similarity	NPC329910
0.86	High Similarity	NPC29410
0.8598	High Similarity	NPC329953
0.8586	High Similarity	NPC470385
0.8586	High Similarity	NPC475118
0.8586	High Similarity	NPC47853
0.8586	High Similarity	NPC470386
0.8585	High Similarity	NPC469744
0.8571	High Similarity	NPC61071
0.8558	High Similarity	NPC101842
0.8545	High Similarity	NPC218970
0.8544	High Similarity	NPC275990
0.8529	High Similarity	NPC287676
0.8519	High Similarity	NPC472719
0.8519	High Similarity	NPC207845
0.8505	High Similarity	NPC98069
0.8505	High Similarity	NPC49730
0.85	High Similarity	NPC98639
0.85	High Similarity	NPC470229
0.8491	Intermediate Similarity	NPC469729
0.8491	Intermediate Similarity	NPC469733
0.8476	Intermediate Similarity	NPC4115
0.8476	Intermediate Similarity	NPC12823
0.8462	Intermediate Similarity	NPC87927
0.8447	Intermediate Similarity	NPC289148
0.8447	Intermediate Similarity	NPC163963
0.8447	Intermediate Similarity	NPC52899
0.8447	Intermediate Similarity	NPC471790
0.8431	Intermediate Similarity	NPC78427
0.8431	Intermediate Similarity	NPC38471
0.8431	Intermediate Similarity	NPC20479
0.8431	Intermediate Similarity	NPC98837
0.8431	Intermediate Similarity	NPC38296
0.8431	Intermediate Similarity	NPC162459
0.8431	Intermediate Similarity	NPC28864
0.8431	Intermediate Similarity	NPC16911
0.8431	Intermediate Similarity	NPC89099
0.8426	Intermediate Similarity	NPC274833
0.8426	Intermediate Similarity	NPC11035
0.8416	Intermediate Similarity	NPC104568
0.8416	Intermediate Similarity	NPC470387
0.8416	Intermediate Similarity	NPC256227
0.8411	Intermediate Similarity	NPC8431
0.8384	Intermediate Similarity	NPC211403
0.8384	Intermediate Similarity	NPC250753
0.8384	Intermediate Similarity	NPC198242
0.8381	Intermediate Similarity	NPC13149
0.8378	Intermediate Similarity	NPC470171
0.8365	Intermediate Similarity	NPC76866
0.8365	Intermediate Similarity	NPC286519
0.8365	Intermediate Similarity	NPC470172
0.8365	Intermediate Similarity	NPC304832
0.8365	Intermediate Similarity	NPC214946
0.8365	Intermediate Similarity	NPC471254
0.8365	Intermediate Similarity	NPC88203
0.8365	Intermediate Similarity	NPC148628
0.8365	Intermediate Similarity	NPC246736
0.835	Intermediate Similarity	NPC293866
0.8349	Intermediate Similarity	NPC470543
0.8333	Intermediate Similarity	NPC10864
0.8288	Intermediate Similarity	NPC472718
0.8286	Intermediate Similarity	NPC159442
0.8286	Intermediate Similarity	NPC471253
0.8286	Intermediate Similarity	NPC216114
0.8286	Intermediate Similarity	NPC473406
0.8273	Intermediate Similarity	NPC146563
0.8265	Intermediate Similarity	NPC56413
0.8257	Intermediate Similarity	NPC272242
0.8257	Intermediate Similarity	NPC201992
0.8252	Intermediate Similarity	NPC469725
0.8241	Intermediate Similarity	NPC473844
0.8241	Intermediate Similarity	NPC91583
0.8241	Intermediate Similarity	NPC240125
0.8241	Intermediate Similarity	NPC51947
0.8235	Intermediate Similarity	NPC13949
0.8224	Intermediate Similarity	NPC471246
0.8224	Intermediate Similarity	NPC176949
0.8224	Intermediate Similarity	NPC201908
0.8208	Intermediate Similarity	NPC84928
0.8208	Intermediate Similarity	NPC96268
0.8208	Intermediate Similarity	NPC98603
0.82	Intermediate Similarity	NPC470230
0.8198	Intermediate Similarity	NPC54395
0.8182	Intermediate Similarity	NPC471043
0.8182	Intermediate Similarity	NPC11252
0.8182	Intermediate Similarity	NPC243572
0.8182	Intermediate Similarity	NPC289312
0.8182	Intermediate Similarity	NPC476964
0.8173	Intermediate Similarity	NPC291785
0.8173	Intermediate Similarity	NPC477655
0.8173	Intermediate Similarity	NPC127408
0.8173	Intermediate Similarity	NPC477656
0.8165	Intermediate Similarity	NPC100908
0.8165	Intermediate Similarity	NPC474567
0.8163	Intermediate Similarity	NPC259009
0.8158	Intermediate Similarity	NPC476961
0.8155	Intermediate Similarity	NPC96839
0.8148	Intermediate Similarity	NPC88744
0.8142	Intermediate Similarity	NPC297179
0.8142	Intermediate Similarity	NPC204552
0.8142	Intermediate Similarity	NPC239293
0.8142	Intermediate Similarity	NPC188667
0.8137	Intermediate Similarity	NPC41070
0.8137	Intermediate Similarity	NPC210214
0.8131	Intermediate Similarity	NPC285927
0.8131	Intermediate Similarity	NPC102352
0.8125	Intermediate Similarity	NPC44170
0.8125	Intermediate Similarity	NPC469823
0.8125	Intermediate Similarity	NPC469820
0.8125	Intermediate Similarity	NPC137414

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 NPC56656 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	272
0.1-0.2	2326
0.2-0.3	3957
0.3-0.4	1685
0.4-0.5	463
0.5-0.6	252
0.6-0.7	156
0.7-0.8	37
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7818	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7797	Intermediate Similarity	NPD8328	Phase 3
0.7788	Intermediate Similarity	NPD8133	Approved
0.7748	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD6319	Approved
0.767	Intermediate Similarity	NPD8034	Phase 2
0.767	Intermediate Similarity	NPD8035	Phase 2
0.7632	Intermediate Similarity	NPD4632	Approved
0.7586	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD6009	Approved
0.7583	Intermediate Similarity	NPD7492	Approved
0.7568	Intermediate Similarity	NPD6412	Phase 2
0.7542	Intermediate Similarity	NPD6054	Approved
0.7541	Intermediate Similarity	NPD7736	Approved
0.7521	Intermediate Similarity	NPD6616	Approved
0.748	Intermediate Similarity	NPD7319	Approved
0.7479	Intermediate Similarity	NPD6016	Approved
0.7479	Intermediate Similarity	NPD6015	Approved
0.7459	Intermediate Similarity	NPD7078	Approved
0.7436	Intermediate Similarity	NPD7115	Discovery
0.7426	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD5988	Approved
0.7417	Intermediate Similarity	NPD6370	Approved
0.7395	Intermediate Similarity	NPD6059	Approved
0.7377	Intermediate Similarity	NPD7507	Approved
0.7345	Intermediate Similarity	NPD6686	Approved
0.7317	Intermediate Similarity	NPD8293	Discontinued
0.7264	Intermediate Similarity	NPD6399	Phase 3
0.7257	Intermediate Similarity	NPD5697	Approved
0.7241	Intermediate Similarity	NPD8297	Approved
0.7241	Intermediate Similarity	NPD6882	Approved
0.7217	Intermediate Similarity	NPD4634	Approved
0.7193	Intermediate Similarity	NPD6899	Approved
0.7193	Intermediate Similarity	NPD6011	Approved
0.7193	Intermediate Similarity	NPD6881	Approved
0.719	Intermediate Similarity	NPD5983	Phase 2
0.7168	Intermediate Similarity	NPD5739	Approved
0.7168	Intermediate Similarity	NPD6008	Approved
0.7168	Intermediate Similarity	NPD6675	Approved
0.7168	Intermediate Similarity	NPD6402	Approved
0.7168	Intermediate Similarity	NPD7128	Approved
0.7156	Intermediate Similarity	NPD7902	Approved
0.7155	Intermediate Similarity	NPD6650	Approved
0.7155	Intermediate Similarity	NPD6649	Approved
0.713	Intermediate Similarity	NPD6373	Approved
0.713	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD6372	Approved
0.713	Intermediate Similarity	NPD6013	Approved
0.713	Intermediate Similarity	NPD6014	Approved
0.713	Intermediate Similarity	NPD6012	Approved
0.7105	Intermediate Similarity	NPD5701	Approved
0.7091	Intermediate Similarity	NPD7638	Approved
0.7091	Intermediate Similarity	NPD4225	Approved
0.708	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD7604	Phase 2
0.7069	Intermediate Similarity	NPD6883	Approved
0.7069	Intermediate Similarity	NPD7102	Approved
0.7069	Intermediate Similarity	NPD7290	Approved
0.7049	Intermediate Similarity	NPD6921	Approved
0.7043	Intermediate Similarity	NPD7320	Approved
0.7037	Intermediate Similarity	NPD7748	Approved
0.7027	Intermediate Similarity	NPD7640	Approved
0.7027	Intermediate Similarity	NPD7639	Approved
0.7025	Intermediate Similarity	NPD7516	Approved
0.7019	Intermediate Similarity	NPD3618	Phase 1
0.7009	Intermediate Similarity	NPD6869	Approved
0.7009	Intermediate Similarity	NPD6847	Approved
0.7009	Intermediate Similarity	NPD7515	Phase 2
0.7009	Intermediate Similarity	NPD8130	Phase 1
0.7009	Intermediate Similarity	NPD6079	Approved
0.7009	Intermediate Similarity	NPD6617	Approved
0.6984	Remote Similarity	NPD6033	Approved
0.6981	Remote Similarity	NPD5328	Approved
0.6967	Remote Similarity	NPD8377	Approved
0.6967	Remote Similarity	NPD8294	Approved
0.696	Remote Similarity	NPD6336	Discontinued
0.6942	Remote Similarity	NPD7328	Approved
0.6942	Remote Similarity	NPD7327	Approved
0.6923	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6911	Remote Similarity	NPD8380	Approved
0.6911	Remote Similarity	NPD8335	Approved
0.6911	Remote Similarity	NPD8033	Approved
0.6911	Remote Similarity	NPD8379	Approved
0.6911	Remote Similarity	NPD8296	Approved
0.6911	Remote Similarity	NPD8378	Approved
0.6909	Remote Similarity	NPD5221	Approved
0.6909	Remote Similarity	NPD5222	Approved
0.6909	Remote Similarity	NPD4697	Phase 3
0.6909	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.69	Remote Similarity	NPD6114	Approved
0.69	Remote Similarity	NPD6115	Approved
0.69	Remote Similarity	NPD6118	Approved
0.69	Remote Similarity	NPD6697	Approved
0.6881	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD7900	Approved
0.6875	Remote Similarity	NPD5286	Approved
0.6875	Remote Similarity	NPD5285	Approved
0.6875	Remote Similarity	NPD4696	Approved
0.6864	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD5173	Approved
0.6847	Remote Similarity	NPD4755	Approved
0.6814	Remote Similarity	NPD5223	Approved
0.68	Remote Similarity	NPD6116	Phase 1
0.6792	Remote Similarity	NPD3573	Approved
0.6789	Remote Similarity	NPD4202	Approved
0.6777	Remote Similarity	NPD6274	Approved
0.6774	Remote Similarity	NPD7503	Approved
0.6774	Remote Similarity	NPD8513	Phase 3
0.6774	Remote Similarity	NPD8516	Approved
0.6774	Remote Similarity	NPD8517	Approved
0.6774	Remote Similarity	NPD8515	Approved
0.6754	Remote Similarity	NPD5224	Approved
0.6754	Remote Similarity	NPD5211	Phase 2
0.6754	Remote Similarity	NPD5226	Approved
0.6754	Remote Similarity	NPD5225	Approved
0.6754	Remote Similarity	NPD4633	Approved
0.6731	Remote Similarity	NPD4788	Approved
0.6726	Remote Similarity	NPD4700	Approved
0.6721	Remote Similarity	NPD6317	Approved
0.67	Remote Similarity	NPD6117	Approved
0.6698	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD5174	Approved
0.6696	Remote Similarity	NPD5175	Approved
0.6696	Remote Similarity	NPD6083	Phase 2
0.6696	Remote Similarity	NPD6084	Phase 2
0.6667	Remote Similarity	NPD6314	Approved
0.6667	Remote Similarity	NPD6335	Approved
0.6667	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6067	Discontinued
0.6667	Remote Similarity	NPD6313	Approved
0.6667	Remote Similarity	NPD4786	Approved
0.664	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD6868	Approved
0.6638	Remote Similarity	NPD5141	Approved
0.6637	Remote Similarity	NPD5696	Approved
0.6635	Remote Similarity	NPD3667	Approved
0.6613	Remote Similarity	NPD7100	Approved
0.6613	Remote Similarity	NPD7101	Approved
0.6609	Remote Similarity	NPD7632	Discontinued
0.66	Remote Similarity	NPD3703	Phase 2
0.6574	Remote Similarity	NPD6672	Approved
0.6574	Remote Similarity	NPD5737	Approved
0.6574	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD4754	Approved
0.6545	Remote Similarity	NPD6411	Approved
0.6542	Remote Similarity	NPD7334	Approved
0.6542	Remote Similarity	NPD6409	Approved
0.6542	Remote Similarity	NPD7521	Approved
0.6542	Remote Similarity	NPD6684	Approved
0.6542	Remote Similarity	NPD5330	Approved
0.6542	Remote Similarity	NPD7146	Approved
0.6538	Remote Similarity	NPD1780	Approved
0.6538	Remote Similarity	NPD1779	Approved
0.6522	Remote Similarity	NPD1700	Approved
0.6518	Remote Similarity	NPD5695	Phase 3
0.6518	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD3665	Phase 1
0.6509	Remote Similarity	NPD3133	Approved
0.6509	Remote Similarity	NPD3666	Approved
0.65	Remote Similarity	NPD6371	Approved
0.65	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD5956	Approved
0.6471	Remote Similarity	NPD4729	Approved
0.6471	Remote Similarity	NPD4730	Approved
0.6471	Remote Similarity	NPD5128	Approved
0.6441	Remote Similarity	NPD4768	Approved
0.6441	Remote Similarity	NPD4767	Approved
0.6436	Remote Similarity	NPD3702	Approved
0.6422	Remote Similarity	NPD6903	Approved
0.6415	Remote Similarity	NPD3669	Approved
0.6415	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6397	Remote Similarity	NPD6334	Approved
0.6397	Remote Similarity	NPD6333	Approved
0.6396	Remote Similarity	NPD5281	Approved
0.6396	Remote Similarity	NPD5284	Approved
0.6385	Remote Similarity	NPD8074	Phase 3
0.6378	Remote Similarity	NPD6908	Approved
0.6378	Remote Similarity	NPD6909	Approved
0.6372	Remote Similarity	NPD5210	Approved
0.6372	Remote Similarity	NPD4629	Approved
0.6371	Remote Similarity	NPD6940	Discontinued
0.6364	Remote Similarity	NPD4753	Phase 2
0.6364	Remote Similarity	NPD6101	Approved
0.6364	Remote Similarity	NPD5247	Approved
0.6364	Remote Similarity	NPD5248	Approved
0.6364	Remote Similarity	NPD5135	Approved
0.6364	Remote Similarity	NPD5169	Approved
0.6364	Remote Similarity	NPD5250	Approved
0.6364	Remote Similarity	NPD5249	Phase 3
0.6364	Remote Similarity	NPD5251	Approved
0.6364	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6339	Remote Similarity	NPD8171	Discontinued
0.6333	Remote Similarity	NPD5168	Approved
0.6311	Remote Similarity	NPD5217	Approved
0.6311	Remote Similarity	NPD5127	Approved
0.6311	Remote Similarity	NPD5215	Approved
0.6311	Remote Similarity	NPD5216	Approved
0.6311	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.63	Remote Similarity	NPD4809	Clinical (unspecified phase)

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