NPASS Compound

Structure

CID9878 OpenBabel06191715332D 37 40 0 0 1 0 0 0 0 0999 V2000 3.5825 5.8323 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6421 5.3445 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9332 -0.9469 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9332 0.0287 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4581 -1.9225 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6132 -1.4347 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5825 4.8567 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6421 4.3689 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4274 4.3689 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2028 3.8811 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8926 0.9543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2723 2.9055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6421 2.4177 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9973 1.2771 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3671 0.7893 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4274 3.3933 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.2028 2.9055 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5825 1.9299 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0477 1.4421 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6005 0.3858 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9703 -0.1020 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.5825 2.9055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0477 2.4177 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4274 1.4421 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2028 0.9543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0883 -0.4591 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4581 -0.9469 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2723 1.9299 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6421 1.4421 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.7375 3.3933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8926 2.9055 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6005 -1.3040 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4337 -0.9469 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8457 2.7192 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2155 2.2314 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6302 0.4878 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 7 2 0 0 0 0 2 8 2 0 0 0 0 3 26 1 0 0 0 0 4 26 1 0 0 0 0 5 27 1 0 0 0 0 6 27 1 0 0 0 0 7 9 1 0 0 0 0 8 10 1 0 0 0 0 11 18 1 0 0 0 0 11 19 1 0 0 0 0 12 16 1 0 0 0 0 12 28 1 0 0 0 0 13 17 1 0 0 0 0 13 29 1 0 0 0 0 14 20 1 0 0 0 0 14 28 1 0 0 0 0 15 21 1 0 0 0 0 15 29 1 0 0 0 0 16 9 1 1 0 0 0 16 22 1 0 0 0 0 17 10 1 6 0 0 0 17 23 1 0 0 0 0 18 22 1 0 0 0 0 18 24 2 0 0 0 0 19 23 1 0 0 0 0 19 25 2 0 0 0 0 20 26 1 6 0 0 0 20 36 1 0 0 0 0 21 27 1 1 0 0 0 21 37 1 0 0 0 0 22 30 2 0 0 0 0 23 31 2 0 0 0 0 24 28 1 0 0 0 0 24 36 1 0 0 0 0 25 29 1 0 0 0 0 25 37 1 0 0 0 0 26 32 1 0 0 0 0 27 33 1 0 0 0 0 28 34 1 1 0 0 0 29 35 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	516.27
Volume:	530.417
LogP:	3.259
LogD:	2.512
LogS:	-4.396
# Rotatable Bonds:	8
TPSA:	133.52
# H-Bond Aceptor:	8
# H-Bond Donor:	4
# Rings:	4
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.362
Synthetic Accessibility Score:	5.728
Fsp3:	0.655
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.683
MDCK Permeability:	0.00011710305261658505
Pgp-inhibitor:	0.07
Pgp-substrate:	0.167
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.032
30% Bioavailability (F30%):	0.066

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.286
Plasma Protein Binding (PPB):	83.71837615966797%
Volume Distribution (VD):	0.501
Pgp-substrate:	6.2069621086120605%

ADMET: Metabolism

CYP1A2-inhibitor:	0.005
CYP1A2-substrate:	0.119
CYP2C19-inhibitor:	0.061
CYP2C19-substrate:	0.665
CYP2C9-inhibitor:	0.374
CYP2C9-substrate:	0.126
CYP2D6-inhibitor:	0.058
CYP2D6-substrate:	0.087
CYP3A4-inhibitor:	0.897
CYP3A4-substrate:	0.868

ADMET: Excretion

Clearance (CL):	4.6
Half-life (T1/2):	0.066

ADMET: Toxicity

hERG Blockers:	0.026
Human Hepatotoxicity (H-HT):	0.208
Drug-inuced Liver Injury (DILI):	0.096
AMES Toxicity:	0.04
Rat Oral Acute Toxicity:	0.651
Maximum Recommended Daily Dose:	0.976
Skin Sensitization:	0.361
Carcinogencity:	0.941
Eye Corrosion:	0.003
Eye Irritation:	0.014
Respiratory Toxicity:	0.926

Download Data

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

Natural Product: NPC9878

Natural Product ID:	NPC9878
*Common Name:**	Illicidione C
IUPAC Name:	(2R,3aS,5S)-7-[[(2R,3aS,5S)-3a-hydroxy-2-(2-hydroxypropan-2-yl)-6-oxo-5-prop-2-enyl-2,3,4,5-tetrahydro-1-benzofuran-7-yl]methyl]-3a-hydroxy-2-(2-hydroxypropan-2-yl)-5-prop-2-enyl-2,3,4,5-tetrahydro-1-benzofuran-6-one
Synonyms:	Illicidione C
Standard InCHIKey:	UPWQUNLKHQUUMH-ZKFBBMPRSA-N
Standard InCHI:	InChI=1S/C29H40O8/c1-7-9-16-12-28(34)14-20(26(3,4)32)36-24(28)18(22(16)30)11-19-23(31)17(10-8-2)13-29(35)15-21(27(5,6)33)37-25(19)29/h7-8,16-17,20-21,32-35H,1-2,9-15H2,3-6H3/t16-,17-,20+,21+,28-,29-/m0/s1
SMILES:	C=CC[C@H]1C[C@@]2(C[C@H](C(C)(C)O)OC2=C(CC2=C3[C@](C[C@H](CC=C)C2=O)(C[C@H](C(C)(C)O)O3)O)C1=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1784753
PubChem CID:	53262723
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
NPO31423	Illicium oligandrum	Species	Schisandraceae	Eukaryota	pericarps	n.a.	n.a.	PMID[19159273]
NPO31423	Illicium oligandrum	Species	Schisandraceae	Eukaryota	stem bark	n.a.	n.a.	PMID[19496609]
NPO31423	Illicium oligandrum	Species	Schisandraceae	Eukaryota	n.a.	stem	n.a.	PMID[21524101]
NPO31423	Illicium oligandrum	Species	Schisandraceae	Eukaryota	n.a.	root	n.a.	PMID[25966312]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
Others	1

Activity Type	# Activity
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	25.3	%	PMID[495363]

☑ 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 NPC9878 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	198
0.1-0.2	1069
0.2-0.3	4415
0.3-0.4	8695
0.4-0.5	16029
0.5-0.6	8401
0.6-0.7	3608
0.7-0.8	274
0.8-0.85	4
0.85-0.9	2
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8947	High Similarity	NPC14322
0.8817	High Similarity	NPC228415
0.8817	High Similarity	NPC87189
0.8182	Intermediate Similarity	NPC469819
0.8182	Intermediate Similarity	NPC114162
0.8058	Intermediate Similarity	NPC471401
0.802	Intermediate Similarity	NPC93271
0.802	Intermediate Similarity	NPC135576
0.7925	Intermediate Similarity	NPC471332
0.7925	Intermediate Similarity	NPC471333
0.781	Intermediate Similarity	NPC70369
0.78	Intermediate Similarity	NPC476705
0.7767	Intermediate Similarity	NPC27105
0.7706	Intermediate Similarity	NPC471400
0.77	Intermediate Similarity	NPC158388
0.77	Intermediate Similarity	NPC478003
0.77	Intermediate Similarity	NPC478004
0.7692	Intermediate Similarity	NPC472687
0.7692	Intermediate Similarity	NPC471330
0.7692	Intermediate Similarity	NPC471331
0.7692	Intermediate Similarity	NPC203388
0.7692	Intermediate Similarity	NPC99657
0.7664	Intermediate Similarity	NPC472756
0.7664	Intermediate Similarity	NPC470104
0.7658	Intermediate Similarity	NPC207251
0.7573	Intermediate Similarity	NPC36954
0.757	Intermediate Similarity	NPC475321
0.7549	Intermediate Similarity	NPC476300
0.7549	Intermediate Similarity	NPC61275
0.7547	Intermediate Similarity	NPC476134
0.7547	Intermediate Similarity	NPC477871
0.7547	Intermediate Similarity	NPC477870
0.7547	Intermediate Similarity	NPC476246
0.7547	Intermediate Similarity	NPC101067
0.7547	Intermediate Similarity	NPC476213
0.7525	Intermediate Similarity	NPC265856
0.7525	Intermediate Similarity	NPC166554
0.7524	Intermediate Similarity	NPC472729
0.7524	Intermediate Similarity	NPC153776
0.7524	Intermediate Similarity	NPC472730
0.7524	Intermediate Similarity	NPC177680
0.7522	Intermediate Similarity	NPC326542
0.75	Intermediate Similarity	NPC476706
0.75	Intermediate Similarity	NPC476707
0.75	Intermediate Similarity	NPC476708
0.75	Intermediate Similarity	NPC8803
0.7477	Intermediate Similarity	NPC476126
0.7477	Intermediate Similarity	NPC223834
0.7477	Intermediate Similarity	NPC476235
0.7477	Intermediate Similarity	NPC99760
0.7474	Intermediate Similarity	NPC291260
0.7459	Intermediate Similarity	NPC102316
0.7453	Intermediate Similarity	NPC472727
0.7453	Intermediate Similarity	NPC472728
0.7451	Intermediate Similarity	NPC146852
0.7431	Intermediate Similarity	NPC472751
0.7431	Intermediate Similarity	NPC472749
0.7429	Intermediate Similarity	NPC124246
0.7429	Intermediate Similarity	NPC40812
0.7429	Intermediate Similarity	NPC20066
0.7429	Intermediate Similarity	NPC239895
0.7411	Intermediate Similarity	NPC38159
0.7396	Intermediate Similarity	NPC472948
0.7387	Intermediate Similarity	NPC101018
0.7383	Intermediate Similarity	NPC15993
0.7379	Intermediate Similarity	NPC475912
0.7379	Intermediate Similarity	NPC179746
0.7379	Intermediate Similarity	NPC81419
0.7368	Intermediate Similarity	NPC247069
0.7358	Intermediate Similarity	NPC255592
0.7358	Intermediate Similarity	NPC187268
0.7358	Intermediate Similarity	NPC83895
0.7358	Intermediate Similarity	NPC300584
0.7358	Intermediate Similarity	NPC187761
0.7358	Intermediate Similarity	NPC261377
0.7358	Intermediate Similarity	NPC308567
0.7353	Intermediate Similarity	NPC473448
0.7353	Intermediate Similarity	NPC51004
0.735	Intermediate Similarity	NPC109973
0.7345	Intermediate Similarity	NPC66108
0.7339	Intermediate Similarity	NPC472748
0.7333	Intermediate Similarity	NPC476315
0.7333	Intermediate Similarity	NPC472733
0.7333	Intermediate Similarity	NPC21681
0.7333	Intermediate Similarity	NPC472734
0.7333	Intermediate Similarity	NPC472675
0.7327	Intermediate Similarity	NPC476704
0.7321	Intermediate Similarity	NPC5103
0.7315	Intermediate Similarity	NPC149371
0.7315	Intermediate Similarity	NPC324017
0.7315	Intermediate Similarity	NPC320019
0.7315	Intermediate Similarity	NPC472754
0.7308	Intermediate Similarity	NPC477241
0.7304	Intermediate Similarity	NPC266728
0.7304	Intermediate Similarity	NPC49492
0.7282	Intermediate Similarity	NPC475441
0.7282	Intermediate Similarity	NPC208886
0.7282	Intermediate Similarity	NPC30515
0.7282	Intermediate Similarity	NPC184463
0.7282	Intermediate Similarity	NPC12172
0.7281	Intermediate Similarity	NPC469463
0.7281	Intermediate Similarity	NPC250109
0.7281	Intermediate Similarity	NPC317210
0.7281	Intermediate Similarity	NPC469454
0.7281	Intermediate Similarity	NPC469496
0.7264	Intermediate Similarity	NPC266842
0.7264	Intermediate Similarity	NPC472731
0.7264	Intermediate Similarity	NPC472732
0.7258	Intermediate Similarity	NPC168879
0.7257	Intermediate Similarity	NPC188738
0.7257	Intermediate Similarity	NPC304180
0.7257	Intermediate Similarity	NPC179798
0.7255	Intermediate Similarity	NPC307411
0.725	Intermediate Similarity	NPC476729
0.7248	Intermediate Similarity	NPC472747
0.7248	Intermediate Similarity	NPC472750
0.7248	Intermediate Similarity	NPC472755
0.7241	Intermediate Similarity	NPC471146
0.7241	Intermediate Similarity	NPC471145
0.7238	Intermediate Similarity	NPC270013
0.7238	Intermediate Similarity	NPC14961
0.7232	Intermediate Similarity	NPC470257
0.7228	Intermediate Similarity	NPC472007
0.7228	Intermediate Similarity	NPC23622
0.7228	Intermediate Similarity	NPC179659
0.7222	Intermediate Similarity	NPC185141
0.7222	Intermediate Similarity	NPC110443
0.7222	Intermediate Similarity	NPC128733
0.7222	Intermediate Similarity	NPC472753
0.7222	Intermediate Similarity	NPC46998
0.7222	Intermediate Similarity	NPC476270
0.7222	Intermediate Similarity	NPC47880
0.7222	Intermediate Similarity	NPC133907
0.7217	Intermediate Similarity	NPC474181
0.7217	Intermediate Similarity	NPC117712
0.7212	Intermediate Similarity	NPC288240
0.7212	Intermediate Similarity	NPC273579
0.7212	Intermediate Similarity	NPC162205
0.7212	Intermediate Similarity	NPC295204
0.7207	Intermediate Similarity	NPC83744
0.72	Intermediate Similarity	NPC475206
0.7196	Intermediate Similarity	NPC306908
0.7193	Intermediate Similarity	NPC472002
0.7193	Intermediate Similarity	NPC236217
0.7184	Intermediate Similarity	NPC469464
0.7184	Intermediate Similarity	NPC179394
0.7184	Intermediate Similarity	NPC474761
0.7184	Intermediate Similarity	NPC476004
0.7184	Intermediate Similarity	NPC144133
0.7184	Intermediate Similarity	NPC471399
0.7182	Intermediate Similarity	NPC220964
0.7182	Intermediate Similarity	NPC255309
0.7182	Intermediate Similarity	NPC475676
0.7182	Intermediate Similarity	NPC100487
0.7182	Intermediate Similarity	NPC146731
0.7179	Intermediate Similarity	NPC106644
0.7179	Intermediate Similarity	NPC234522
0.717	Intermediate Similarity	NPC279621
0.7168	Intermediate Similarity	NPC286880
0.7167	Intermediate Similarity	NPC18945
0.7167	Intermediate Similarity	NPC91693
0.7167	Intermediate Similarity	NPC105926
0.7167	Intermediate Similarity	NPC265557
0.7157	Intermediate Similarity	NPC472008
0.7156	Intermediate Similarity	NPC183571
0.7156	Intermediate Similarity	NPC86077
0.7155	Intermediate Similarity	NPC54739
0.7143	Intermediate Similarity	NPC472001
0.7143	Intermediate Similarity	NPC81386
0.7143	Intermediate Similarity	NPC474035
0.7143	Intermediate Similarity	NPC473288
0.7143	Intermediate Similarity	NPC196227
0.7143	Intermediate Similarity	NPC474338
0.7143	Intermediate Similarity	NPC471999
0.7143	Intermediate Similarity	NPC472000
0.7143	Intermediate Similarity	NPC329417
0.7143	Intermediate Similarity	NPC168883
0.7131	Intermediate Similarity	NPC152091
0.713	Intermediate Similarity	NPC471204
0.713	Intermediate Similarity	NPC241221
0.713	Intermediate Similarity	NPC474271
0.713	Intermediate Similarity	NPC54705
0.713	Intermediate Similarity	NPC962
0.713	Intermediate Similarity	NPC56448
0.7129	Intermediate Similarity	NPC472009
0.7117	Intermediate Similarity	NPC49958
0.7117	Intermediate Similarity	NPC97202
0.7117	Intermediate Similarity	NPC214264
0.7117	Intermediate Similarity	NPC302607
0.7117	Intermediate Similarity	NPC50692
0.7117	Intermediate Similarity	NPC319077
0.7117	Intermediate Similarity	NPC296945
0.7117	Intermediate Similarity	NPC202167
0.7117	Intermediate Similarity	NPC223450
0.7117	Intermediate Similarity	NPC152695
0.7117	Intermediate Similarity	NPC476027
0.7117	Intermediate Similarity	NPC85829
0.7117	Intermediate Similarity	NPC48733
0.7117	Intermediate Similarity	NPC150531
0.7117	Intermediate Similarity	NPC253223

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 NPC9878 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	1525
0.2-0.3	3934
0.3-0.4	2463
0.4-0.5	681
0.5-0.6	290
0.6-0.7	87
0.7-0.8	2
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
0.7308	Intermediate Similarity	NPD5282	Discontinued
0.7172	Intermediate Similarity	NPD6110	Phase 1
0.7019	Intermediate Similarity	NPD46	Approved
0.7019	Intermediate Similarity	NPD6698	Approved
0.6952	Remote Similarity	NPD7983	Approved
0.6903	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD5778	Approved
0.6887	Remote Similarity	NPD5779	Approved
0.681	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD6053	Discontinued
0.6696	Remote Similarity	NPD6686	Approved
0.6667	Remote Similarity	NPD7154	Phase 3
0.6609	Remote Similarity	NPD6412	Phase 2
0.6581	Remote Similarity	NPD6371	Approved
0.6577	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD4250	Approved
0.6571	Remote Similarity	NPD4251	Approved
0.6542	Remote Similarity	NPD7838	Discovery
0.6529	Remote Similarity	NPD7115	Discovery
0.6512	Remote Similarity	NPD7260	Phase 2
0.6504	Remote Similarity	NPD6054	Approved
0.6476	Remote Similarity	NPD4249	Approved
0.6471	Remote Similarity	NPD8297	Approved
0.6455	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD5210	Approved
0.6455	Remote Similarity	NPD4629	Approved
0.6452	Remote Similarity	NPD8513	Phase 3
0.6452	Remote Similarity	NPD8515	Approved
0.6452	Remote Similarity	NPD8516	Approved
0.6452	Remote Similarity	NPD8517	Approved
0.6441	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD4225	Approved
0.6429	Remote Similarity	NPD5696	Approved
0.6404	Remote Similarity	NPD5211	Phase 2
0.64	Remote Similarity	NPD6370	Approved
0.6387	Remote Similarity	NPD6650	Approved
0.6387	Remote Similarity	NPD6649	Approved
0.6383	Remote Similarity	NPD7331	Phase 2
0.6371	Remote Similarity	NPD6059	Approved
0.6371	Remote Similarity	NPD6319	Approved
0.6356	Remote Similarity	NPD6372	Approved
0.6356	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6356	Remote Similarity	NPD6373	Approved
0.6336	Remote Similarity	NPD6845	Suspended
0.6321	Remote Similarity	NPD4519	Discontinued
0.6321	Remote Similarity	NPD4623	Approved
0.632	Remote Similarity	NPD6016	Approved
0.632	Remote Similarity	NPD6015	Approved
0.6316	Remote Similarity	NPD5344	Discontinued
0.6306	Remote Similarity	NPD5695	Phase 3
0.6303	Remote Similarity	NPD4634	Approved
0.6299	Remote Similarity	NPD7492	Approved
0.6296	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD6101	Approved
0.6293	Remote Similarity	NPD5141	Approved
0.6281	Remote Similarity	NPD4632	Approved
0.6277	Remote Similarity	NPD7341	Phase 2
0.6273	Remote Similarity	NPD6399	Phase 3
0.6271	Remote Similarity	NPD7320	Approved
0.6271	Remote Similarity	NPD6899	Approved
0.6271	Remote Similarity	NPD6881	Approved
0.627	Remote Similarity	NPD5988	Approved
0.6262	Remote Similarity	NPD7524	Approved
0.625	Remote Similarity	NPD7507	Approved
0.625	Remote Similarity	NPD6616	Approved
0.625	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6435	Approved
0.625	Remote Similarity	NPD7839	Suspended
0.6239	Remote Similarity	NPD6675	Approved
0.6239	Remote Similarity	NPD6008	Approved
0.6239	Remote Similarity	NPD5739	Approved
0.6239	Remote Similarity	NPD6402	Approved
0.6239	Remote Similarity	NPD7128	Approved
0.6228	Remote Similarity	NPD5286	Approved
0.6228	Remote Similarity	NPD5285	Approved
0.6228	Remote Similarity	NPD4696	Approved
0.6226	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6226	Remote Similarity	NPD1694	Approved
0.6226	Remote Similarity	NPD5363	Approved
0.6218	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6202	Remote Similarity	NPD8074	Phase 3
0.6202	Remote Similarity	NPD7078	Approved
0.6198	Remote Similarity	NPD6882	Approved
0.6195	Remote Similarity	NPD6083	Phase 2
0.6195	Remote Similarity	NPD7902	Approved
0.6195	Remote Similarity	NPD6084	Phase 2
0.6195	Remote Similarity	NPD4755	Approved
0.619	Remote Similarity	NPD5362	Discontinued
0.6186	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD5697	Approved
0.6182	Remote Similarity	NPD5281	Approved
0.6182	Remote Similarity	NPD6411	Approved
0.6182	Remote Similarity	NPD5284	Approved
0.6182	Remote Similarity	NPD6079	Approved
0.6168	Remote Similarity	NPD3618	Phase 1
0.6168	Remote Similarity	NPD5786	Approved
0.6168	Remote Similarity	NPD5279	Phase 3
0.6167	Remote Similarity	NPD6883	Approved
0.6167	Remote Similarity	NPD7102	Approved
0.6167	Remote Similarity	NPD7290	Approved
0.6154	Remote Similarity	NPD7736	Approved
0.6147	Remote Similarity	NPD5328	Approved
0.6147	Remote Similarity	NPD4753	Phase 2
0.6134	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6132	Remote Similarity	NPD3665	Phase 1
0.6132	Remote Similarity	NPD3133	Approved
0.6132	Remote Similarity	NPD3666	Approved
0.6121	Remote Similarity	NPD4633	Approved
0.6121	Remote Similarity	NPD5226	Approved
0.6121	Remote Similarity	NPD5224	Approved
0.6121	Remote Similarity	NPD5225	Approved
0.6116	Remote Similarity	NPD6847	Approved
0.6116	Remote Similarity	NPD6869	Approved
0.6116	Remote Similarity	NPD6617	Approved
0.6116	Remote Similarity	NPD8130	Phase 1
0.6107	Remote Similarity	NPD7319	Approved
0.6095	Remote Similarity	NPD4269	Approved
0.6095	Remote Similarity	NPD4270	Approved
0.6094	Remote Similarity	NPD8328	Phase 3
0.6091	Remote Similarity	NPD5785	Approved
0.6091	Remote Similarity	NPD5207	Approved
0.6087	Remote Similarity	NPD7640	Approved
0.6087	Remote Similarity	NPD6648	Approved
0.6087	Remote Similarity	NPD7639	Approved
0.6087	Remote Similarity	NPD4700	Approved
0.6083	Remote Similarity	NPD6012	Approved
0.6083	Remote Similarity	NPD6014	Approved
0.6083	Remote Similarity	NPD6013	Approved
0.6077	Remote Similarity	NPD8293	Discontinued
0.6071	Remote Similarity	NPD7748	Approved
0.6068	Remote Similarity	NPD5174	Approved
0.6068	Remote Similarity	NPD5175	Approved
0.6063	Remote Similarity	NPD7503	Approved
0.6058	Remote Similarity	NPD4820	Approved
0.6058	Remote Similarity	NPD4819	Approved
0.6058	Remote Similarity	NPD4821	Approved
0.6058	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6058	Remote Similarity	NPD4822	Approved
0.6058	Remote Similarity	NPD5368	Approved
0.6058	Remote Similarity	NPD4695	Discontinued
0.6055	Remote Similarity	NPD6903	Approved
0.605	Remote Similarity	NPD5701	Approved
0.6034	Remote Similarity	NPD5223	Approved
0.6029	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD5690	Phase 2
0.6019	Remote Similarity	NPD7521	Approved
0.6019	Remote Similarity	NPD6409	Approved
0.6019	Remote Similarity	NPD7334	Approved
0.6019	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD6684	Approved
0.6019	Remote Similarity	NPD7146	Approved
0.6019	Remote Similarity	NPD5330	Approved
0.6018	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6	Remote Similarity	NPD1695	Approved
0.6	Remote Similarity	NPD6011	Approved
0.6	Remote Similarity	NPD6009	Approved
0.6	Remote Similarity	NPD4729	Approved
0.6	Remote Similarity	NPD4730	Approved
0.6	Remote Similarity	NPD5369	Approved
0.6	Remote Similarity	NPD7638	Approved
0.5982	Remote Similarity	NPD4202	Approved
0.5981	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5981	Remote Similarity	NPD4786	Approved
0.5969	Remote Similarity	NPD7604	Phase 2
0.5966	Remote Similarity	NPD4768	Approved
0.5966	Remote Similarity	NPD4767	Approved
0.5965	Remote Similarity	NPD4697	Phase 3
0.5965	Remote Similarity	NPD5221	Approved
0.5965	Remote Similarity	NPD5222	Approved
0.5965	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5952	Remote Similarity	NPD7641	Discontinued
0.5943	Remote Similarity	NPD4221	Approved
0.5943	Remote Similarity	NPD4223	Phase 3
0.5943	Remote Similarity	NPD3667	Approved
0.5943	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5938	Remote Similarity	NPD5983	Phase 2
0.5929	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5929	Remote Similarity	NPD7900	Approved
0.5926	Remote Similarity	NPD5329	Approved
0.5923	Remote Similarity	NPD8299	Approved
0.5923	Remote Similarity	NPD8342	Approved
0.5923	Remote Similarity	NPD8340	Approved
0.5923	Remote Similarity	NPD8341	Approved
0.5922	Remote Similarity	NPD4756	Discovery
0.5913	Remote Similarity	NPD5173	Approved
0.5909	Remote Similarity	NPD6033	Approved
0.5909	Remote Similarity	NPD6672	Approved
0.5909	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD5737	Approved
0.5906	Remote Similarity	NPD7516	Approved
0.5905	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.5905	Remote Similarity	NPD4252	Approved
0.5902	Remote Similarity	NPD5247	Approved
0.5902	Remote Similarity	NPD5248	Approved
0.5902	Remote Similarity	NPD5249	Phase 3
0.5902	Remote Similarity	NPD5250	Approved
0.5902	Remote Similarity	NPD5251	Approved
0.5893	Remote Similarity	NPD7515	Phase 2
0.5893	Remote Similarity	NPD7637	Suspended
0.5891	Remote Similarity	NPD8080	Discontinued

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