NPASS Compound

Structure

NPC149371 OpenBabel07101719512D 30 31 0 0 1 0 0 0 0 0999 V2000 -0.7488 -6.3554 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8116 1.2518 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1646 -4.3991 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8364 -2.4487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4172 -4.2300 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7344 -3.3749 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0056 -5.6862 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4697 -0.2263 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8765 -1.1399 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6092 0.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6037 0.2737 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.2135 -4.7081 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3364 -1.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4661 -4.5390 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 3.6685 -2.1180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6581 -1.4781 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0649 -2.3917 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.9309 -2.8917 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5296 -4.0390 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7431 -0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9254 -2.7872 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.2582 -5.5171 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5346 -2.6180 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4807 -4.3480 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7213 -0.4612 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8209 -3.7817 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7230 -3.8698 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 0.3217 -3.0608 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 7 1 0 0 0 0 3 12 1 0 0 0 0 4 13 2 0 0 0 0 5 14 1 0 0 0 0 7 12 2 0 0 0 0 8 9 2 0 0 0 0 8 11 1 0 0 0 0 9 16 1 0 0 0 0 10 11 1 0 0 0 0 11 2 1 1 0 0 0 12 20 1 0 0 0 0 13 21 1 0 0 0 0 14 23 2 0 0 0 0 14 28 1 0 0 0 0 15 10 1 6 0 0 0 15 17 1 0 0 0 0 15 29 1 0 0 0 0 16 22 1 0 0 0 0 16 24 2 0 0 0 0 17 13 1 1 0 0 0 17 18 1 0 0 0 0 18 19 1 0 0 0 0 18 30 1 1 0 0 0 19 22 1 6 0 0 0 19 28 1 0 0 0 0 20 25 2 0 0 0 0 20 30 1 0 0 0 0 21 26 2 0 0 0 0 21 29 1 0 0 0 0 22 6 1 1 0 0 0 22 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	420.18
Volume:	423.822
LogP:	1.621
LogD:	0.979
LogS:	-2.946
# Rotatable Bonds:	5
TPSA:	116.2
# H-Bond Aceptor:	8
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.319
Synthetic Accessibility Score:	5.183
Fsp3:	0.545
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.718
MDCK Permeability:	2.329367634956725e-05
Pgp-inhibitor:	0.396
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.623
20% Bioavailability (F20%):	0.284
30% Bioavailability (F30%):	0.914

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.693
Plasma Protein Binding (PPB):	53.72819519042969%
Volume Distribution (VD):	1.206
Pgp-substrate:	26.805587768554688%

ADMET: Metabolism

CYP1A2-inhibitor:	0.156
CYP1A2-substrate:	0.084
CYP2C19-inhibitor:	0.48
CYP2C19-substrate:	0.098
CYP2C9-inhibitor:	0.517
CYP2C9-substrate:	0.069
CYP2D6-inhibitor:	0.278
CYP2D6-substrate:	0.051
CYP3A4-inhibitor:	0.558
CYP3A4-substrate:	0.229

ADMET: Excretion

Clearance (CL):	5.836
Half-life (T1/2):	0.913

ADMET: Toxicity

hERG Blockers:	0.007
Human Hepatotoxicity (H-HT):	0.793
Drug-inuced Liver Injury (DILI):	0.882
AMES Toxicity:	0.046
Rat Oral Acute Toxicity:	0.647
Maximum Recommended Daily Dose:	0.106
Skin Sensitization:	0.703
Carcinogencity:	0.615
Eye Corrosion:	0.021
Eye Irritation:	0.144
Respiratory Toxicity:	0.391

Download Data

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

Natural Product: NPC149371

Natural Product ID:	NPC149371
*Common Name:**	Calein C
IUPAC Name:	[(3aS,4S,5R,6R,8Z,10R,11aR)-5-acetyloxy-6-hydroxy-6,10-dimethyl-3-methylidene-2,7-dioxo-3a,4,5,10,11,11a-hexahydrocyclodeca[b]furan-4-yl] (E)-2-methylbut-2-enoate
Synonyms:	Calein C
Standard InCHIKey:	DXPFQBFCOCKNEU-RMCHFIGYSA-N
Standard InCHI:	InChI=1S/C22H28O8/c1-7-12(3)20(25)30-18-17-13(4)21(26)29-15(17)10-11(2)8-9-16(24)22(6,27)19(18)28-14(5)23/h7-9,11,15,17-19,27H,4,10H2,1-3,5-6H3/b9-8-,12-7+/t11-,15+,17-,18-,19+,22-/m0/s1
SMILES:	C/C=C(C)/C(=O)O[C@H]1[C@H]2C(=C)C(=O)O[C@@H]2C[C@@H](C)/C=CC(=O)[C@@](C)([C@@H]1OC(=O)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2047550
PubChem CID:	66551442
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001543] Sesquiterpene lactones [CHEMONTID:0001771] Germacranolides and derivatives

*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
NPO33370	brickellia cavanillesii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22587572]

☑ 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	2
Ki	1

Activity Type	# Activity
Individual Protein	1
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1648	Individual Protein	Oligo-1,6-glucosidase	Saccharomyces cerevisiae S288c	IC50	=	280000.0	nM	PMID[463102]
NPT2	Others	Unspecified		IC50	=	280000.0	nM	PMID[463101]
NPT2	Others	Unspecified		Ki	=	410000.0	nM	PMID[463101]

☑ 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 NPC149371 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	226
0.1-0.2	1278
0.2-0.3	4599
0.3-0.4	8111
0.4-0.5	14410
0.5-0.6	8246
0.6-0.7	4148
0.7-0.8	1393
0.8-0.85	188
0.85-0.9	85
0.9-0.95	11
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9894	High Similarity	NPC47880
0.9474	High Similarity	NPC471144
0.9286	High Similarity	NPC475945
0.9286	High Similarity	NPC475871
0.9278	High Similarity	NPC474339
0.9278	High Similarity	NPC474742
0.9278	High Similarity	NPC164598
0.92	High Similarity	NPC477513
0.9192	High Similarity	NPC474741
0.9184	High Similarity	NPC474747
0.899	High Similarity	NPC472754
0.898	High Similarity	NPC288876
0.898	High Similarity	NPC475949
0.8958	High Similarity	NPC475659
0.8958	High Similarity	NPC471142
0.8947	High Similarity	NPC476300
0.89	High Similarity	NPC472755
0.89	High Similarity	NPC475873
0.8889	High Similarity	NPC472753
0.8889	High Similarity	NPC477511
0.8889	High Similarity	NPC264477
0.8889	High Similarity	NPC201718
0.8889	High Similarity	NPC15993
0.8866	High Similarity	NPC470883
0.8866	High Similarity	NPC17585
0.8866	High Similarity	NPC39859
0.8866	High Similarity	NPC473859
0.8866	High Similarity	NPC76862
0.8866	High Similarity	NPC158416
0.8812	High Similarity	NPC472756
0.8812	High Similarity	NPC477510
0.8812	High Similarity	NPC471143
0.88	High Similarity	NPC471148
0.88	High Similarity	NPC320019
0.88	High Similarity	NPC324017
0.8788	High Similarity	NPC477512
0.8763	High Similarity	NPC36954
0.875	High Similarity	NPC162205
0.875	High Similarity	NPC475912
0.875	High Similarity	NPC273579
0.875	High Similarity	NPC295204
0.875	High Similarity	NPC288240
0.8737	High Similarity	NPC144133
0.8737	High Similarity	NPC179394
0.8737	High Similarity	NPC51004
0.8737	High Similarity	NPC473619
0.8713	High Similarity	NPC4620
0.87	High Similarity	NPC110443
0.87	High Similarity	NPC133907
0.87	High Similarity	NPC46998
0.87	High Similarity	NPC476270
0.87	High Similarity	NPC128733
0.87	High Similarity	NPC185141
0.8687	High Similarity	NPC473326
0.8673	High Similarity	NPC279621
0.8673	High Similarity	NPC476009
0.8673	High Similarity	NPC230800
0.8673	High Similarity	NPC477921
0.866	High Similarity	NPC190294
0.8654	High Similarity	NPC38154
0.8646	High Similarity	NPC30515
0.8646	High Similarity	NPC184463
0.8646	High Similarity	NPC473321
0.8632	High Similarity	NPC307411
0.8627	High Similarity	NPC220964
0.8627	High Similarity	NPC100487
0.8627	High Similarity	NPC475676
0.8627	High Similarity	NPC203659
0.8586	High Similarity	NPC40812
0.8586	High Similarity	NPC471140
0.8571	High Similarity	NPC270013
0.8571	High Similarity	NPC475900
0.8571	High Similarity	NPC471141
0.8571	High Similarity	NPC477922
0.8571	High Similarity	NPC14961
0.8557	High Similarity	NPC475302
0.8557	High Similarity	NPC212486
0.8557	High Similarity	NPC179746
0.8557	High Similarity	NPC81419
0.8557	High Similarity	NPC469645
0.8557	High Similarity	NPC469692
0.8544	High Similarity	NPC16313
0.8544	High Similarity	NPC9303
0.8542	High Similarity	NPC475855
0.8529	High Similarity	NPC110989
0.8526	High Similarity	NPC202672
0.8485	Intermediate Similarity	NPC31645
0.8485	Intermediate Similarity	NPC476315
0.8469	Intermediate Similarity	NPC303942
0.8469	Intermediate Similarity	NPC57405
0.8469	Intermediate Similarity	NPC81386
0.8469	Intermediate Similarity	NPC473316
0.8469	Intermediate Similarity	NPC474247
0.8469	Intermediate Similarity	NPC121825
0.8469	Intermediate Similarity	NPC471147
0.8469	Intermediate Similarity	NPC474035
0.8469	Intermediate Similarity	NPC140543
0.8469	Intermediate Similarity	NPC473330
0.8462	Intermediate Similarity	NPC326994
0.8462	Intermediate Similarity	NPC474421
0.8462	Intermediate Similarity	NPC72813
0.8462	Intermediate Similarity	NPC324327
0.8462	Intermediate Similarity	NPC26617
0.8462	Intermediate Similarity	NPC194620
0.8454	Intermediate Similarity	NPC12172
0.8454	Intermediate Similarity	NPC208886
0.8454	Intermediate Similarity	NPC20713
0.8447	Intermediate Similarity	NPC472748
0.844	Intermediate Similarity	NPC471146
0.844	Intermediate Similarity	NPC471145
0.8438	Intermediate Similarity	NPC166919
0.8438	Intermediate Similarity	NPC151770
0.8438	Intermediate Similarity	NPC474032
0.8431	Intermediate Similarity	NPC225353
0.8411	Intermediate Similarity	NPC66108
0.84	Intermediate Similarity	NPC328562
0.84	Intermediate Similarity	NPC323421
0.8381	Intermediate Similarity	NPC233379
0.8381	Intermediate Similarity	NPC474664
0.8381	Intermediate Similarity	NPC169888
0.8381	Intermediate Similarity	NPC14862
0.8381	Intermediate Similarity	NPC55972
0.8381	Intermediate Similarity	NPC327286
0.8367	Intermediate Similarity	NPC125674
0.8367	Intermediate Similarity	NPC228451
0.8367	Intermediate Similarity	NPC475838
0.8365	Intermediate Similarity	NPC475802
0.8365	Intermediate Similarity	NPC472751
0.8365	Intermediate Similarity	NPC472749
0.8351	Intermediate Similarity	NPC474232
0.8351	Intermediate Similarity	NPC475748
0.8351	Intermediate Similarity	NPC474761
0.8351	Intermediate Similarity	NPC476004
0.835	Intermediate Similarity	NPC472747
0.835	Intermediate Similarity	NPC472750
0.8333	Intermediate Similarity	NPC473715
0.8317	Intermediate Similarity	NPC261377
0.8317	Intermediate Similarity	NPC208233
0.8317	Intermediate Similarity	NPC187761
0.8317	Intermediate Similarity	NPC255592
0.8317	Intermediate Similarity	NPC308567
0.8317	Intermediate Similarity	NPC83895
0.8317	Intermediate Similarity	NPC161855
0.8317	Intermediate Similarity	NPC474213
0.8302	Intermediate Similarity	NPC15218
0.83	Intermediate Similarity	NPC35498
0.8283	Intermediate Similarity	NPC476267
0.8265	Intermediate Similarity	NPC111114
0.8265	Intermediate Similarity	NPC300312
0.8265	Intermediate Similarity	NPC261607
0.8252	Intermediate Similarity	NPC183571
0.8229	Intermediate Similarity	NPC231889
0.8224	Intermediate Similarity	NPC5103
0.8218	Intermediate Similarity	NPC471462
0.82	Intermediate Similarity	NPC474947
0.819	Intermediate Similarity	NPC223450
0.8182	Intermediate Similarity	NPC165383
0.8173	Intermediate Similarity	NPC474165
0.8173	Intermediate Similarity	NPC69171
0.8163	Intermediate Similarity	NPC251385
0.8163	Intermediate Similarity	NPC49342
0.8148	Intermediate Similarity	NPC179798
0.8148	Intermediate Similarity	NPC304180
0.8144	Intermediate Similarity	NPC476803
0.8144	Intermediate Similarity	NPC476805
0.8144	Intermediate Similarity	NPC475819
0.8137	Intermediate Similarity	NPC187268
0.8131	Intermediate Similarity	NPC42662
0.8131	Intermediate Similarity	NPC475922
0.8125	Intermediate Similarity	NPC469483
0.8125	Intermediate Similarity	NPC305475
0.8125	Intermediate Similarity	NPC50637
0.8125	Intermediate Similarity	NPC475461
0.8125	Intermediate Similarity	NPC469910
0.8119	Intermediate Similarity	NPC473291
0.8119	Intermediate Similarity	NPC476275
0.81	Intermediate Similarity	NPC469632
0.8061	Intermediate Similarity	NPC474951
0.8061	Intermediate Similarity	NPC92974
0.8061	Intermediate Similarity	NPC295312
0.8061	Intermediate Similarity	NPC173926
0.8056	Intermediate Similarity	NPC161816
0.8056	Intermediate Similarity	NPC115257
0.8056	Intermediate Similarity	NPC477103
0.8041	Intermediate Similarity	NPC160138
0.8041	Intermediate Similarity	NPC266957
0.8041	Intermediate Similarity	NPC186148
0.8041	Intermediate Similarity	NPC179659
0.8037	Intermediate Similarity	NPC475960
0.8036	Intermediate Similarity	NPC475401
0.8021	Intermediate Similarity	NPC38468
0.8021	Intermediate Similarity	NPC21469
0.8021	Intermediate Similarity	NPC470755
0.8021	Intermediate Similarity	NPC50362
0.8021	Intermediate Similarity	NPC255307
0.8021	Intermediate Similarity	NPC261380
0.8021	Intermediate Similarity	NPC319795
0.802	Intermediate Similarity	NPC304886
0.8019	Intermediate Similarity	NPC243998
0.8	Intermediate Similarity	NPC469463

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 NPC149371 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	205
0.1-0.2	1851
0.2-0.3	3621
0.3-0.4	2215
0.4-0.5	830
0.5-0.6	294
0.6-0.7	122
0.7-0.8	11
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8462	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.8021	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.79	Intermediate Similarity	NPD7983	Approved
0.7843	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.78	Intermediate Similarity	NPD46	Approved
0.78	Intermediate Similarity	NPD6698	Approved
0.7727	Intermediate Similarity	NPD6371	Approved
0.7624	Intermediate Similarity	NPD7838	Discovery
0.7573	Intermediate Similarity	NPD5282	Discontinued
0.75	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6319	Approved
0.713	Intermediate Similarity	NPD4225	Approved
0.713	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD5785	Approved
0.7083	Intermediate Similarity	NPD8515	Approved
0.7083	Intermediate Similarity	NPD8517	Approved
0.7083	Intermediate Similarity	NPD8516	Approved
0.7083	Intermediate Similarity	NPD8513	Phase 3
0.708	Intermediate Similarity	NPD6686	Approved
0.7019	Intermediate Similarity	NPD1695	Approved
0.6981	Remote Similarity	NPD5778	Approved
0.6981	Remote Similarity	NPD5779	Approved
0.6977	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD7642	Approved
0.6961	Remote Similarity	NPD5363	Approved
0.693	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD5786	Approved
0.6891	Remote Similarity	NPD7115	Discovery
0.6847	Remote Similarity	NPD5344	Discontinued
0.68	Remote Similarity	NPD8074	Phase 3
0.6789	Remote Similarity	NPD7839	Suspended
0.678	Remote Similarity	NPD4632	Approved
0.6774	Remote Similarity	NPD7492	Approved
0.6733	Remote Similarity	NPD5369	Approved
0.6721	Remote Similarity	NPD6054	Approved
0.672	Remote Similarity	NPD6616	Approved
0.6719	Remote Similarity	NPD7260	Phase 2
0.6695	Remote Similarity	NPD8297	Approved
0.6695	Remote Similarity	NPD6053	Discontinued
0.6694	Remote Similarity	NPD7829	Approved
0.6694	Remote Similarity	NPD7830	Approved
0.6667	Remote Similarity	NPD6435	Approved
0.6667	Remote Similarity	NPD7078	Approved
0.6667	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4270	Approved
0.6667	Remote Similarity	NPD6015	Approved
0.6667	Remote Similarity	NPD4269	Approved
0.6667	Remote Similarity	NPD6016	Approved
0.6635	Remote Similarity	NPD1694	Approved
0.6614	Remote Similarity	NPD7736	Approved
0.6613	Remote Similarity	NPD6370	Approved
0.6613	Remote Similarity	NPD5988	Approved
0.661	Remote Similarity	NPD6649	Approved
0.661	Remote Similarity	NPD6650	Approved
0.6607	Remote Similarity	NPD6648	Approved
0.6602	Remote Similarity	NPD7154	Phase 3
0.6587	Remote Similarity	NPD8451	Approved
0.6571	Remote Similarity	NPD4249	Approved
0.6562	Remote Similarity	NPD7319	Approved
0.656	Remote Similarity	NPD8328	Phase 3
0.6557	Remote Similarity	NPD7641	Discontinued
0.6552	Remote Similarity	NPD5697	Approved
0.6542	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD6101	Approved
0.6535	Remote Similarity	NPD8448	Approved
0.6532	Remote Similarity	NPD8444	Approved
0.6525	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6525	Remote Similarity	NPD4634	Approved
0.6509	Remote Similarity	NPD4250	Approved
0.6509	Remote Similarity	NPD4251	Approved
0.6505	Remote Similarity	NPD5209	Approved
0.6496	Remote Similarity	NPD6881	Approved
0.6496	Remote Similarity	NPD6899	Approved
0.648	Remote Similarity	NPD8080	Discontinued
0.6475	Remote Similarity	NPD6009	Approved
0.6471	Remote Similarity	NPD2204	Approved
0.6471	Remote Similarity	NPD4252	Approved
0.6471	Remote Similarity	NPD5368	Approved
0.6457	Remote Similarity	NPD7507	Approved
0.6452	Remote Similarity	NPD6059	Approved
0.6442	Remote Similarity	NPD6110	Phase 1
0.6441	Remote Similarity	NPD6014	Approved
0.6441	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6441	Remote Similarity	NPD6013	Approved
0.6441	Remote Similarity	NPD6372	Approved
0.6441	Remote Similarity	NPD6373	Approved
0.6441	Remote Similarity	NPD6012	Approved
0.6422	Remote Similarity	NPD6411	Approved
0.6417	Remote Similarity	NPD6882	Approved
0.6412	Remote Similarity	NPD6845	Suspended
0.6406	Remote Similarity	NPD8293	Discontinued
0.64	Remote Similarity	NPD5983	Phase 2
0.64	Remote Similarity	NPD6921	Approved
0.6387	Remote Similarity	NPD7102	Approved
0.6387	Remote Similarity	NPD6883	Approved
0.6387	Remote Similarity	NPD7290	Approved
0.6385	Remote Similarity	NPD8390	Approved
0.6385	Remote Similarity	NPD8392	Approved
0.6385	Remote Similarity	NPD8391	Approved
0.6378	Remote Similarity	NPD8340	Approved
0.6378	Remote Similarity	NPD8299	Approved
0.6378	Remote Similarity	NPD8342	Approved
0.6378	Remote Similarity	NPD8341	Approved
0.6356	Remote Similarity	NPD6011	Approved
0.6346	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6341	Remote Similarity	NPD7500	Approved
0.6333	Remote Similarity	NPD8130	Phase 1
0.6333	Remote Similarity	NPD6617	Approved
0.6333	Remote Similarity	NPD6847	Approved
0.6333	Remote Similarity	NPD6869	Approved
0.6328	Remote Similarity	NPD8273	Phase 1
0.6325	Remote Similarity	NPD7128	Approved
0.6325	Remote Similarity	NPD5739	Approved
0.6325	Remote Similarity	NPD6402	Approved
0.6325	Remote Similarity	NPD6008	Approved
0.6325	Remote Similarity	NPD6675	Approved
0.6311	Remote Similarity	NPD4820	Approved
0.6311	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD4819	Approved
0.6311	Remote Similarity	NPD4821	Approved
0.6311	Remote Similarity	NPD4822	Approved
0.6299	Remote Similarity	NPD7604	Phase 2
0.6286	Remote Similarity	NPD5362	Discontinued
0.6271	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6271	Remote Similarity	NPD5701	Approved
0.627	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.625	Remote Similarity	NPD5695	Phase 3
0.6228	Remote Similarity	NPD5696	Approved
0.6228	Remote Similarity	NPD7638	Approved
0.6218	Remote Similarity	NPD7320	Approved
0.621	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD5211	Phase 2
0.6202	Remote Similarity	NPD6336	Discontinued
0.6194	Remote Similarity	NPD8415	Approved
0.6176	Remote Similarity	NPD4756	Discovery
0.6174	Remote Similarity	NPD5285	Approved
0.6174	Remote Similarity	NPD7640	Approved
0.6174	Remote Similarity	NPD7639	Approved
0.6174	Remote Similarity	NPD5286	Approved
0.6174	Remote Similarity	NPD4696	Approved
0.6168	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6148	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.614	Remote Similarity	NPD6083	Phase 2
0.614	Remote Similarity	NPD6084	Phase 2
0.6134	Remote Similarity	NPD6412	Phase 2
0.6126	Remote Similarity	NPD7637	Suspended
0.6117	Remote Similarity	NPD4271	Approved
0.6117	Remote Similarity	NPD4268	Approved
0.6117	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6102	Remote Similarity	NPD5141	Approved
0.6091	Remote Similarity	NPD5370	Suspended
0.608	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD6399	Phase 3
0.6068	Remote Similarity	NPD4633	Approved
0.6068	Remote Similarity	NPD5225	Approved
0.6068	Remote Similarity	NPD5224	Approved
0.6068	Remote Similarity	NPD5226	Approved
0.6042	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6017	Remote Similarity	NPD5174	Approved
0.6017	Remote Similarity	NPD5175	Approved
0.6016	Remote Similarity	NPD8266	Approved
0.6016	Remote Similarity	NPD8267	Approved
0.6016	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6016	Remote Similarity	NPD7503	Approved
0.6016	Remote Similarity	NPD8268	Approved
0.6016	Remote Similarity	NPD8269	Approved
0.6015	Remote Similarity	NPD5956	Approved
0.6	Remote Similarity	NPD6274	Approved
0.6	Remote Similarity	NPD4755	Approved
0.5985	Remote Similarity	NPD6033	Approved
0.5984	Remote Similarity	NPD7101	Approved
0.5984	Remote Similarity	NPD2067	Discontinued
0.5984	Remote Similarity	NPD7100	Approved
0.5983	Remote Similarity	NPD5223	Approved
0.5982	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.5982	Remote Similarity	NPD5693	Phase 1
0.5979	Remote Similarity	NPD7331	Phase 2
0.5965	Remote Similarity	NPD5210	Approved
0.5965	Remote Similarity	NPD4629	Approved
0.5952	Remote Similarity	NPD6317	Approved
0.595	Remote Similarity	NPD4729	Approved
0.595	Remote Similarity	NPD4730	Approved
0.5938	Remote Similarity	NPD3197	Phase 1
0.5935	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.5935	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5913	Remote Similarity	NPD5221	Approved
0.5913	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5913	Remote Similarity	NPD5222	Approved
0.5906	Remote Similarity	NPD6314	Approved
0.5906	Remote Similarity	NPD6313	Approved
0.5906	Remote Similarity	NPD7328	Approved
0.5906	Remote Similarity	NPD7327	Approved
0.5906	Remote Similarity	NPD6335	Approved
0.5897	Remote Similarity	NPD4700	Approved
0.5891	Remote Similarity	NPD8033	Approved
0.5876	Remote Similarity	NPD7341	Phase 2
0.5862	Remote Similarity	NPD7902	Approved
0.5862	Remote Similarity	NPD5173	Approved
0.5859	Remote Similarity	NPD4522	Approved
0.5859	Remote Similarity	NPD7516	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