NPASS Compound

Structure

CID247069 OpenBabel06191716052D 36 40 0 0 1 0 0 0 0 0999 V2000 2.8912 -4.4850 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0883 -3.0214 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8736 2.3885 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8736 1.4131 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3324 0.3570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8201 -0.4877 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3789 -3.6403 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5115 -2.1425 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8912 -2.7956 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0380 -1.3366 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.9508 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2237 -0.4877 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8093 0.1650 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8447 -1.4631 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8447 -1.4631 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.2237 -1.4631 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3789 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2061 1.0561 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6895 -1.9508 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6895 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8447 -0.4877 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5342 -1.4631 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0107 -0.5413 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7184 1.9008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8447 -0.4877 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5342 -0.4877 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3789 -1.9508 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0107 -1.4095 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6895 -1.9508 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0684 -1.9508 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7470 0.3051 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2061 2.7455 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8666 -2.7956 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4612 -2.2154 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1761 0.9541 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 24 1 0 0 0 0 4 24 1 0 0 0 0 5 25 1 0 0 0 0 6 25 1 0 0 0 0 7 9 1 0 0 0 0 8 10 1 0 0 0 0 9 27 1 0 0 0 0 10 28 1 0 0 0 0 11 14 1 0 0 0 0 11 15 1 0 0 0 0 12 16 1 0 0 0 0 12 17 2 0 0 0 0 13 18 1 0 0 0 0 14 19 1 0 0 0 0 14 21 2 0 0 0 0 15 25 1 0 0 0 0 15 29 1 1 0 0 0 16 27 1 0 0 0 0 16 30 2 0 0 0 0 17 26 1 0 0 0 0 17 35 1 0 0 0 0 18 24 1 1 0 0 0 18 35 1 0 0 0 0 19 22 1 0 0 0 0 19 28 1 1 0 0 0 20 21 1 0 0 0 0 20 23 1 0 0 0 0 20 26 1 6 0 0 0 21 36 1 0 0 0 0 22 26 1 6 0 0 0 22 27 1 0 0 0 0 23 28 1 0 0 0 0 23 31 2 0 0 0 0 24 32 1 0 0 0 0 25 36 1 0 0 0 0 26 13 1 1 0 0 0 27 33 1 6 0 0 0 28 34 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	500.24
Volume:	504.565
LogP:	2.696
LogD:	1.95
LogS:	-3.937
# Rotatable Bonds:	5
TPSA:	133.52
# H-Bond Aceptor:	8
# H-Bond Donor:	4
# Rings:	6
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.421
Synthetic Accessibility Score:	7.027
Fsp3:	0.643
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:	-4.801
MDCK Permeability:	2.654793752299156e-05
Pgp-inhibitor:	0.994
Pgp-substrate:	0.009
Human Intestinal Absorption (HIA):	0.027
20% Bioavailability (F20%):	0.254
30% Bioavailability (F30%):	0.518

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.579
Plasma Protein Binding (PPB):	77.68804168701172%
Volume Distribution (VD):	1.357
Pgp-substrate:	11.33975887298584%

ADMET: Metabolism

CYP1A2-inhibitor:	0.003
CYP1A2-substrate:	0.12
CYP2C19-inhibitor:	0.02
CYP2C19-substrate:	0.631
CYP2C9-inhibitor:	0.018
CYP2C9-substrate:	0.089
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.051
CYP3A4-inhibitor:	0.296
CYP3A4-substrate:	0.825

ADMET: Excretion

Clearance (CL):	1.968
Half-life (T1/2):	0.279

ADMET: Toxicity

hERG Blockers:	0.095
Human Hepatotoxicity (H-HT):	0.203
Drug-inuced Liver Injury (DILI):	0.043
AMES Toxicity:	0.015
Rat Oral Acute Toxicity:	0.561
Maximum Recommended Daily Dose:	0.906
Skin Sensitization:	0.456
Carcinogencity:	0.285
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.894

Download Data

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

Natural Product: NPC247069

Natural Product ID:	NPC247069
*Common Name:**	Illicidione A
IUPAC Name:	n.a.
Synonyms:	Illicidione A
Standard InCHIKey:	MAPMVOGTJVXZRF-FTADZCBISA-N
Standard InCHI:	InChI=1S/C28H36O8/c1-7-9-27(33)16(30)12-17-26(13-18(35-17)24(3,4)32)20-21-14(11-15(29)25(5,6)36-21)19(22(26)27)28(34,10-8-2)23(20)31/h7-8,12,15,18-20,22,29,32-34H,1-2,9-11,13H2,3-6H3/t15-,18+,19+,20+,22-,26+,27+,28-/m1/s1
SMILES:	C=CC[C@]1(O)C(=O)[C@@H]2C3=C([C@H]1[C@@H]1[C@@]42C[C@H](OC4=CC(=O)[C@@]1(O)CC=C)C(O)(C)C)C[C@H](C(O3)(C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1784751
PubChem CID:	54581405
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001640] Naphthopyrans

*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	=	38.2	%	PMID[547756]

☑ 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 NPC247069 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	219
0.1-0.2	1358
0.2-0.3	4308
0.3-0.4	7793
0.4-0.5	12899
0.5-0.6	8584
0.6-0.7	5792
0.7-0.8	1674
0.8-0.85	69
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8761	High Similarity	NPC122033
0.8761	High Similarity	NPC474654
0.8761	High Similarity	NPC287343
0.8761	High Similarity	NPC470854
0.8761	High Similarity	NPC97908
0.8534	High Similarity	NPC478051
0.8522	High Similarity	NPC204552
0.8522	High Similarity	NPC17772
0.8522	High Similarity	NPC188667
0.8522	High Similarity	NPC297179
0.8509	High Similarity	NPC328374
0.8509	High Similarity	NPC40632
0.8509	High Similarity	NPC96312
0.8509	High Similarity	NPC251236
0.8496	Intermediate Similarity	NPC7921
0.8496	Intermediate Similarity	NPC208998
0.8496	Intermediate Similarity	NPC49451
0.8462	Intermediate Similarity	NPC102822
0.8462	Intermediate Similarity	NPC477046
0.8455	Intermediate Similarity	NPC144854
0.8455	Intermediate Similarity	NPC3316
0.8448	Intermediate Similarity	NPC469488
0.8448	Intermediate Similarity	NPC470777
0.844	Intermediate Similarity	NPC40170
0.8421	Intermediate Similarity	NPC473798
0.8396	Intermediate Similarity	NPC27105
0.8393	Intermediate Similarity	NPC210005
0.8378	Intermediate Similarity	NPC154608
0.8378	Intermediate Similarity	NPC192813
0.8378	Intermediate Similarity	NPC277017
0.8376	Intermediate Similarity	NPC112038
0.8364	Intermediate Similarity	NPC471333
0.8364	Intermediate Similarity	NPC471332
0.8362	Intermediate Similarity	NPC251310
0.8348	Intermediate Similarity	NPC207217
0.8348	Intermediate Similarity	NPC134869
0.8348	Intermediate Similarity	NPC16081
0.8348	Intermediate Similarity	NPC152199
0.8348	Intermediate Similarity	NPC173686
0.8348	Intermediate Similarity	NPC235539
0.8333	Intermediate Similarity	NPC198539
0.8319	Intermediate Similarity	NPC146945
0.8319	Intermediate Similarity	NPC171888
0.8319	Intermediate Similarity	NPC265557
0.8319	Intermediate Similarity	NPC105926
0.8319	Intermediate Similarity	NPC18945
0.8319	Intermediate Similarity	NPC91693
0.8318	Intermediate Similarity	NPC472687
0.8318	Intermediate Similarity	NPC99657
0.8318	Intermediate Similarity	NPC471331
0.8318	Intermediate Similarity	NPC203388
0.8318	Intermediate Similarity	NPC471330
0.8304	Intermediate Similarity	NPC470257
0.8304	Intermediate Similarity	NPC20192
0.8276	Intermediate Similarity	NPC470775
0.8276	Intermediate Similarity	NPC176513
0.8261	Intermediate Similarity	NPC143268
0.8261	Intermediate Similarity	NPC18547
0.8261	Intermediate Similarity	NPC45218
0.8261	Intermediate Similarity	NPC323821
0.8261	Intermediate Similarity	NPC474906
0.8261	Intermediate Similarity	NPC268238
0.825	Intermediate Similarity	NPC476729
0.825	Intermediate Similarity	NPC24651
0.8246	Intermediate Similarity	NPC90769
0.8246	Intermediate Similarity	NPC289312
0.8246	Intermediate Similarity	NPC474516
0.8246	Intermediate Similarity	NPC11252
0.8235	Intermediate Similarity	NPC312833
0.8214	Intermediate Similarity	NPC293850
0.8198	Intermediate Similarity	NPC102352
0.8197	Intermediate Similarity	NPC477712
0.8197	Intermediate Similarity	NPC477713
0.8182	Intermediate Similarity	NPC320294
0.8182	Intermediate Similarity	NPC225049
0.8174	Intermediate Similarity	NPC477266
0.8167	Intermediate Similarity	NPC67251
0.8165	Intermediate Similarity	NPC181645
0.8158	Intermediate Similarity	NPC201992
0.8142	Intermediate Similarity	NPC87335
0.8142	Intermediate Similarity	NPC27814
0.8131	Intermediate Similarity	NPC472734
0.8131	Intermediate Similarity	NPC472733
0.8125	Intermediate Similarity	NPC43285
0.8125	Intermediate Similarity	NPC58370
0.812	Intermediate Similarity	NPC477116
0.812	Intermediate Similarity	NPC27999
0.8099	Intermediate Similarity	NPC470922
0.8099	Intermediate Similarity	NPC473255
0.8087	Intermediate Similarity	NPC193948
0.8083	Intermediate Similarity	NPC269642
0.8073	Intermediate Similarity	NPC46761
0.8056	Intermediate Similarity	NPC472732
0.8056	Intermediate Similarity	NPC472731
0.8056	Intermediate Similarity	NPC273269
0.8053	Intermediate Similarity	NPC272576
0.8051	Intermediate Similarity	NPC470776
0.8051	Intermediate Similarity	NPC176005
0.8036	Intermediate Similarity	NPC181357
0.8034	Intermediate Similarity	NPC179626
0.8034	Intermediate Similarity	NPC474734
0.8033	Intermediate Similarity	NPC181999
0.8019	Intermediate Similarity	NPC61275
0.8017	Intermediate Similarity	NPC120724
0.8017	Intermediate Similarity	NPC51978
0.8017	Intermediate Similarity	NPC141196
0.8017	Intermediate Similarity	NPC326264
0.8017	Intermediate Similarity	NPC194100
0.8017	Intermediate Similarity	NPC238005
0.8017	Intermediate Similarity	NPC469789
0.8017	Intermediate Similarity	NPC1980
0.8017	Intermediate Similarity	NPC25909
0.8	Intermediate Similarity	NPC470779
0.8	Intermediate Similarity	NPC474229
0.8	Intermediate Similarity	NPC188738
0.8	Intermediate Similarity	NPC470184
0.8	Intermediate Similarity	NPC476193
0.8	Intermediate Similarity	NPC102316
0.8	Intermediate Similarity	NPC471243
0.8	Intermediate Similarity	NPC46570
0.7984	Intermediate Similarity	NPC221414
0.7983	Intermediate Similarity	NPC473920
0.7983	Intermediate Similarity	NPC473203
0.7983	Intermediate Similarity	NPC476529
0.7983	Intermediate Similarity	NPC268958
0.7983	Intermediate Similarity	NPC475775
0.7982	Intermediate Similarity	NPC153776
0.7982	Intermediate Similarity	NPC141350
0.7982	Intermediate Similarity	NPC177680
0.7982	Intermediate Similarity	NPC472730
0.7982	Intermediate Similarity	NPC472729
0.7967	Intermediate Similarity	NPC470882
0.7967	Intermediate Similarity	NPC473265
0.7967	Intermediate Similarity	NPC476008
0.7966	Intermediate Similarity	NPC469684
0.7966	Intermediate Similarity	NPC473590
0.7965	Intermediate Similarity	NPC202524
0.7963	Intermediate Similarity	NPC91439
0.7951	Intermediate Similarity	NPC8369
0.7949	Intermediate Similarity	NPC261330
0.7946	Intermediate Similarity	NPC475036
0.7946	Intermediate Similarity	NPC96268
0.7934	Intermediate Similarity	NPC23786
0.7934	Intermediate Similarity	NPC470265
0.7934	Intermediate Similarity	NPC107493
0.7934	Intermediate Similarity	NPC222688
0.7931	Intermediate Similarity	NPC269530
0.7931	Intermediate Similarity	NPC472002
0.7931	Intermediate Similarity	NPC205534
0.7928	Intermediate Similarity	NPC478176
0.7925	Intermediate Similarity	NPC146852
0.7917	Intermediate Similarity	NPC107338
0.7917	Intermediate Similarity	NPC109607
0.7913	Intermediate Similarity	NPC474567
0.7913	Intermediate Similarity	NPC5103
0.7909	Intermediate Similarity	NPC472728
0.7909	Intermediate Similarity	NPC472727
0.7909	Intermediate Similarity	NPC472972
0.7903	Intermediate Similarity	NPC295220
0.7903	Intermediate Similarity	NPC475636
0.7899	Intermediate Similarity	NPC284707
0.7899	Intermediate Similarity	NPC21326
0.789	Intermediate Similarity	NPC20078
0.789	Intermediate Similarity	NPC272451
0.789	Intermediate Similarity	NPC473574
0.7886	Intermediate Similarity	NPC285091
0.7886	Intermediate Similarity	NPC93368
0.7886	Intermediate Similarity	NPC477745
0.7886	Intermediate Similarity	NPC473635
0.7886	Intermediate Similarity	NPC87662
0.7886	Intermediate Similarity	NPC198714
0.7886	Intermediate Similarity	NPC293112
0.7881	Intermediate Similarity	NPC176840
0.7881	Intermediate Similarity	NPC190286
0.7881	Intermediate Similarity	NPC478216
0.7881	Intermediate Similarity	NPC470628
0.7881	Intermediate Similarity	NPC474046
0.7881	Intermediate Similarity	NPC259306
0.7876	Intermediate Similarity	NPC166607
0.7869	Intermediate Similarity	NPC11895
0.7869	Intermediate Similarity	NPC227397
0.7869	Intermediate Similarity	NPC135038
0.7869	Intermediate Similarity	NPC43252
0.7863	Intermediate Similarity	NPC108721
0.7863	Intermediate Similarity	NPC73300
0.7863	Intermediate Similarity	NPC471204
0.7863	Intermediate Similarity	NPC320118
0.7863	Intermediate Similarity	NPC472926
0.7863	Intermediate Similarity	NPC469454
0.7863	Intermediate Similarity	NPC469496
0.7863	Intermediate Similarity	NPC194273
0.7863	Intermediate Similarity	NPC469463
0.7857	Intermediate Similarity	NPC275583
0.7857	Intermediate Similarity	NPC117185
0.7857	Intermediate Similarity	NPC254614
0.7857	Intermediate Similarity	NPC100390
0.7857	Intermediate Similarity	NPC159442
0.7851	Intermediate Similarity	NPC42675
0.7851	Intermediate Similarity	NPC67569
0.7845	Intermediate Similarity	NPC34315

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 NPC247069 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	195
0.1-0.2	1617
0.2-0.3	3903
0.3-0.4	2241
0.4-0.5	709
0.5-0.6	257
0.6-0.7	146
0.7-0.8	82
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
0.7917	Intermediate Similarity	NPD6319	Approved
0.7917	Intermediate Similarity	NPD6054	Approved
0.7787	Intermediate Similarity	NPD6370	Approved
0.7769	Intermediate Similarity	NPD6059	Approved
0.7759	Intermediate Similarity	NPD4634	Approved
0.7724	Intermediate Similarity	NPD8328	Phase 3
0.7712	Intermediate Similarity	NPD4632	Approved
0.7705	Intermediate Similarity	NPD6016	Approved
0.7705	Intermediate Similarity	NPD6015	Approved
0.7661	Intermediate Similarity	NPD7492	Approved
0.7642	Intermediate Similarity	NPD5988	Approved
0.7627	Intermediate Similarity	NPD8297	Approved
0.7619	Intermediate Similarity	NPD7736	Approved
0.7615	Intermediate Similarity	NPD5282	Discontinued
0.76	Intermediate Similarity	NPD6616	Approved
0.7586	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7542	Intermediate Similarity	NPD6649	Approved
0.7542	Intermediate Similarity	NPD6650	Approved
0.754	Intermediate Similarity	NPD7078	Approved
0.7521	Intermediate Similarity	NPD6372	Approved
0.7521	Intermediate Similarity	NPD6373	Approved
0.7521	Intermediate Similarity	NPD7115	Discovery
0.7436	Intermediate Similarity	NPD6881	Approved
0.7436	Intermediate Similarity	NPD6899	Approved
0.7434	Intermediate Similarity	NPD4696	Approved
0.7434	Intermediate Similarity	NPD5286	Approved
0.7434	Intermediate Similarity	NPD5285	Approved
0.7414	Intermediate Similarity	NPD7128	Approved
0.7414	Intermediate Similarity	NPD5739	Approved
0.7414	Intermediate Similarity	NPD6675	Approved
0.7414	Intermediate Similarity	NPD6402	Approved
0.7411	Intermediate Similarity	NPD4755	Approved
0.7402	Intermediate Similarity	NPD8293	Discontinued
0.7377	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7377	Intermediate Similarity	NPD6009	Approved
0.7368	Intermediate Similarity	NPD5223	Approved
0.735	Intermediate Similarity	NPD5697	Approved
0.7344	Intermediate Similarity	NPD6033	Approved
0.7333	Intermediate Similarity	NPD6882	Approved
0.7321	Intermediate Similarity	NPD5221	Approved
0.7321	Intermediate Similarity	NPD5222	Approved
0.7321	Intermediate Similarity	NPD4697	Phase 3
0.7321	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7311	Intermediate Similarity	NPD6883	Approved
0.7311	Intermediate Similarity	NPD7102	Approved
0.7311	Intermediate Similarity	NPD7290	Approved
0.7304	Intermediate Similarity	NPD5224	Approved
0.7304	Intermediate Similarity	NPD5226	Approved
0.7304	Intermediate Similarity	NPD5225	Approved
0.7304	Intermediate Similarity	NPD4633	Approved
0.7304	Intermediate Similarity	NPD5211	Phase 2
0.7302	Intermediate Similarity	NPD7604	Phase 2
0.7288	Intermediate Similarity	NPD6011	Approved
0.7288	Intermediate Similarity	NPD7320	Approved
0.7281	Intermediate Similarity	NPD4700	Approved
0.728	Intermediate Similarity	NPD5983	Phase 2
0.7273	Intermediate Similarity	NPD6079	Approved
0.7265	Intermediate Similarity	NPD6008	Approved
0.7257	Intermediate Similarity	NPD5173	Approved
0.725	Intermediate Similarity	NPD8130	Phase 1
0.725	Intermediate Similarity	NPD6617	Approved
0.725	Intermediate Similarity	NPD6869	Approved
0.725	Intermediate Similarity	NPD6847	Approved
0.7248	Intermediate Similarity	NPD5328	Approved
0.7241	Intermediate Similarity	NPD5175	Approved
0.7241	Intermediate Similarity	NPD5174	Approved
0.7227	Intermediate Similarity	NPD6012	Approved
0.7227	Intermediate Similarity	NPD6013	Approved
0.7227	Intermediate Similarity	NPD6014	Approved
0.7203	Intermediate Similarity	NPD6412	Phase 2
0.7203	Intermediate Similarity	NPD5701	Approved
0.7188	Intermediate Similarity	NPD6336	Discontinued
0.7179	Intermediate Similarity	NPD5141	Approved
0.7143	Intermediate Similarity	NPD4729	Approved
0.7143	Intermediate Similarity	NPD8513	Phase 3
0.7143	Intermediate Similarity	NPD4730	Approved
0.713	Intermediate Similarity	NPD3618	Phase 1
0.7119	Intermediate Similarity	NPD4768	Approved
0.7119	Intermediate Similarity	NPD4767	Approved
0.7107	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD7902	Approved
0.7094	Intermediate Similarity	NPD4754	Approved
0.7083	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD5248	Approved
0.7025	Intermediate Similarity	NPD5250	Approved
0.7025	Intermediate Similarity	NPD5247	Approved
0.7025	Intermediate Similarity	NPD5251	Approved
0.7025	Intermediate Similarity	NPD5249	Phase 3
0.7023	Intermediate Similarity	NPD7319	Approved
0.7008	Intermediate Similarity	NPD8517	Approved
0.7008	Intermediate Similarity	NPD8515	Approved
0.7008	Intermediate Similarity	NPD6921	Approved
0.7008	Intermediate Similarity	NPD8516	Approved
0.6991	Remote Similarity	NPD7748	Approved
0.6964	Remote Similarity	NPD6411	Approved
0.6964	Remote Similarity	NPD7515	Phase 2
0.6942	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7507	Approved
0.6917	Remote Similarity	NPD7260	Phase 2
0.6905	Remote Similarity	NPD6335	Approved
0.6903	Remote Similarity	NPD6399	Phase 3
0.6903	Remote Similarity	NPD4202	Approved
0.6897	Remote Similarity	NPD4225	Approved
0.6885	Remote Similarity	NPD5135	Approved
0.6885	Remote Similarity	NPD5169	Approved
0.6885	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.686	Remote Similarity	NPD5128	Approved
0.685	Remote Similarity	NPD7101	Approved
0.685	Remote Similarity	NPD7100	Approved
0.6842	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD7900	Approved
0.6829	Remote Similarity	NPD5215	Approved
0.6829	Remote Similarity	NPD5217	Approved
0.6829	Remote Similarity	NPD5216	Approved
0.6829	Remote Similarity	NPD5127	Approved
0.6825	Remote Similarity	NPD6317	Approved
0.6818	Remote Similarity	NPD5279	Phase 3
0.6818	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.681	Remote Similarity	NPD6083	Phase 2
0.681	Remote Similarity	NPD6084	Phase 2
0.6789	Remote Similarity	NPD4786	Approved
0.6786	Remote Similarity	NPD4753	Phase 2
0.6786	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD6101	Approved
0.6783	Remote Similarity	NPD4629	Approved
0.6783	Remote Similarity	NPD5695	Phase 3
0.6783	Remote Similarity	NPD5210	Approved
0.6774	Remote Similarity	NPD6053	Discontinued
0.6772	Remote Similarity	NPD6313	Approved
0.6772	Remote Similarity	NPD6314	Approved
0.6759	Remote Similarity	NPD3667	Approved
0.6757	Remote Similarity	NPD3573	Approved
0.6754	Remote Similarity	NPD5779	Approved
0.6754	Remote Similarity	NPD5778	Approved
0.6752	Remote Similarity	NPD7638	Approved
0.6746	Remote Similarity	NPD6274	Approved
0.6746	Remote Similarity	NPD6868	Approved
0.6744	Remote Similarity	NPD7503	Approved
0.6729	Remote Similarity	NPD4695	Discontinued
0.6721	Remote Similarity	NPD5168	Approved
0.6721	Remote Similarity	NPD6686	Approved
0.6695	Remote Similarity	NPD7640	Approved
0.6695	Remote Similarity	NPD7639	Approved
0.6694	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5690	Phase 2
0.6667	Remote Similarity	NPD5167	Approved
0.6641	Remote Similarity	NPD6067	Discontinued
0.6639	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6637	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD3666	Approved
0.6636	Remote Similarity	NPD3665	Phase 1
0.6636	Remote Similarity	NPD3133	Approved
0.6618	Remote Similarity	NPD6845	Suspended
0.6617	Remote Similarity	NPD8074	Phase 3
0.6615	Remote Similarity	NPD6909	Approved
0.6615	Remote Similarity	NPD6908	Approved
0.661	Remote Similarity	NPD5696	Approved
0.6593	Remote Similarity	NPD5956	Approved
0.6589	Remote Similarity	NPD4522	Approved
0.6577	Remote Similarity	NPD5329	Approved
0.6574	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD5737	Approved
0.6549	Remote Similarity	NPD6672	Approved
0.6545	Remote Similarity	NPD6110	Phase 1
0.6522	Remote Similarity	NPD7983	Approved
0.6522	Remote Similarity	NPD5284	Approved
0.6522	Remote Similarity	NPD5281	Approved
0.6518	Remote Similarity	NPD4694	Approved
0.6518	Remote Similarity	NPD5280	Approved
0.6512	Remote Similarity	NPD7328	Approved
0.6512	Remote Similarity	NPD7327	Approved
0.6496	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6496	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD4197	Approved
0.648	Remote Similarity	NPD6371	Approved
0.6462	Remote Similarity	NPD7516	Approved
0.6404	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD3617	Approved
0.6383	Remote Similarity	NPD6333	Approved
0.6383	Remote Similarity	NPD6334	Approved
0.6379	Remote Similarity	NPD8034	Phase 2
0.6379	Remote Similarity	NPD6050	Approved
0.6379	Remote Similarity	NPD8035	Phase 2
0.6379	Remote Similarity	NPD5694	Approved
0.6372	Remote Similarity	NPD7521	Approved
0.6372	Remote Similarity	NPD6409	Approved
0.6372	Remote Similarity	NPD7146	Approved
0.6372	Remote Similarity	NPD6684	Approved
0.6372	Remote Similarity	NPD7334	Approved
0.6372	Remote Similarity	NPD5330	Approved
0.6364	Remote Similarity	NPD5344	Discontinued
0.6364	Remote Similarity	NPD8033	Approved
0.6348	Remote Similarity	NPD6904	Approved
0.6348	Remote Similarity	NPD6080	Approved
0.6348	Remote Similarity	NPD6673	Approved
0.6339	Remote Similarity	NPD3668	Phase 3
0.6328	Remote Similarity	NPD8133	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