NPASS Compound

Structure

NPC474379 OpenBabel07101719512D 35 40 0 0 1 0 0 0 0 0999 V2000 -1.6898 1.9512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0225 -1.5941 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5103 -2.4390 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.9268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5347 -1.4634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 0.9756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8449 -2.4390 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6898 -3.9024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2709 -0.5788 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8449 -3.4146 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6898 -1.9512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9237 -1.3038 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6898 -0.9756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4816 -1.9459 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6898 0.9756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3796 -0.9756 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.0000 -1.9512 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6898 -1.9512 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5347 -3.4146 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8449 -0.4878 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5347 -0.4878 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8449 0.4878 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6898 0.9756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5347 -2.4390 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8449 -2.4390 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6898 -0.9756 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -0.9756 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8449 -0.4878 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5347 0.4878 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3796 -3.9024 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6898 1.9512 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4359 -2.1487 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8449 0.4878 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5347 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 15 1 0 0 0 0 2 24 1 0 0 0 0 3 24 1 0 0 0 0 5 26 1 0 0 0 0 6 27 1 0 0 0 0 7 11 1 0 0 0 0 7 17 1 0 0 0 0 8 10 1 0 0 0 0 8 19 1 0 0 0 0 9 12 1 0 0 0 0 9 16 1 0 0 0 0 10 25 1 0 0 0 0 11 26 1 0 0 0 0 12 32 1 0 0 0 0 13 18 1 0 0 0 0 13 20 1 0 0 0 0 14 16 1 0 0 0 0 14 32 1 0 0 0 0 15 29 2 0 0 0 0 15 33 1 0 0 0 0 16 21 1 0 0 0 0 17 25 1 6 0 0 0 17 27 1 0 0 0 0 18 24 1 0 0 0 0 18 25 1 6 0 0 0 19 24 1 0 0 0 0 19 30 2 0 0 0 0 20 27 1 1 0 0 0 20 33 1 0 0 0 0 21 26 1 1 0 0 0 21 34 1 0 0 0 0 22 23 1 0 0 0 0 22 28 1 1 0 0 0 22 35 1 0 0 0 0 23 31 2 0 0 0 0 23 34 1 0 0 0 0 25 4 1 6 0 0 0 26 28 1 1 0 0 0 27 28 1 1 0 0 0 28 35 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	488.28
Volume:	495.128
LogP:	3.451
LogD:	3.25
LogS:	-4.683
# Rotatable Bonds:	3
TPSA:	91.43
# H-Bond Aceptor:	7
# H-Bond Donor:	0
# Rings:	6
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.431
Synthetic Accessibility Score:	5.553
Fsp3:	0.893
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.269
MDCK Permeability:	2.4737229978200048e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.777
30% Bioavailability (F30%):	0.906

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.752
Plasma Protein Binding (PPB):	71.71144104003906%
Volume Distribution (VD):	1.284
Pgp-substrate:	22.750802993774414%

ADMET: Metabolism

CYP1A2-inhibitor:	0.011
CYP1A2-substrate:	0.431
CYP2C19-inhibitor:	0.04
CYP2C19-substrate:	0.862
CYP2C9-inhibitor:	0.133
CYP2C9-substrate:	0.033
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.193
CYP3A4-inhibitor:	0.52
CYP3A4-substrate:	0.604

ADMET: Excretion

Clearance (CL):	4.847
Half-life (T1/2):	0.363

ADMET: Toxicity

hERG Blockers:	0.013
Human Hepatotoxicity (H-HT):	0.165
Drug-inuced Liver Injury (DILI):	0.365
AMES Toxicity:	0.056
Rat Oral Acute Toxicity:	0.111
Maximum Recommended Daily Dose:	0.446
Skin Sensitization:	0.391
Carcinogencity:	0.061
Eye Corrosion:	0.151
Eye Irritation:	0.394
Respiratory Toxicity:	0.716

Download Data

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

Natural Product: NPC474379

Natural Product ID:	NPC474379
*Common Name:**	Hexahydrogedunin
IUPAC Name:	n.a.
Synonyms:	Hexahydrogedunin
Standard InCHIKey:	ZLMLDQGGOFVZEN-SFLDSBRCSA-N
Standard InCHI:	InChI=1S/C28H40O7/c1-15(29)33-20-13-18-24(2,3)19(30)8-10-25(18,4)17-7-11-26(5)21(16-9-12-32-14-16)34-23(31)22-28(26,35-22)27(17,20)6/h16-18,20-22H,7-14H2,1-6H3/t16?,17-,18+,20-,21+,22-,25-,26+,27+,28-/m1/s1
SMILES:	CC(=O)O[C@@H]1C[C@H]2C(C)(C)C(=O)CC[C@@]2([C@@H]2[C@]1(C)[C@@]13O[C@@H]1C(=O)O[C@H]([C@@]3(CC2)C)C1CCOC1)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL465765
PubChem CID:	10696361
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids [CHEMONTID:0002380] Limonoids

*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
NPO20413	Meliaceae spp.	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9134742]
NPO20413	Meliaceae spp.	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]

☑ 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
Others	3

Activity Type	# Activity
Cell Line	1
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	Activity	=	99.0	%	PMID[478287]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	10.0	ug.mL-1	PMID[478287]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	2.13	ug.mL-1	PMID[478287]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Activity	=	0.39	%	PMID[478287]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Activity	=	0.94	%	PMID[478287]

☑ 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 NPC474379 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	538
0.1-0.2	4173
0.2-0.3	9174
0.3-0.4	13595
0.4-0.5	6008
0.5-0.6	5227
0.6-0.7	3293
0.7-0.8	659
0.8-0.85	28
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8864	High Similarity	NPC477441
0.8791	High Similarity	NPC216137
0.8478	Intermediate Similarity	NPC477433
0.8478	Intermediate Similarity	NPC477444
0.8478	Intermediate Similarity	NPC477442
0.8416	Intermediate Similarity	NPC474242
0.8404	Intermediate Similarity	NPC309127
0.8404	Intermediate Similarity	NPC247877
0.837	Intermediate Similarity	NPC477440
0.837	Intermediate Similarity	NPC477443
0.8295	Intermediate Similarity	NPC329490
0.8295	Intermediate Similarity	NPC328639
0.8229	Intermediate Similarity	NPC163685
0.8229	Intermediate Similarity	NPC235109
0.8222	Intermediate Similarity	NPC65133
0.8222	Intermediate Similarity	NPC477434
0.8211	Intermediate Similarity	NPC477495
0.8182	Intermediate Similarity	NPC125366
0.8172	Intermediate Similarity	NPC67653
0.8172	Intermediate Similarity	NPC471459
0.8125	Intermediate Similarity	NPC82633
0.8111	Intermediate Similarity	NPC476721
0.8105	Intermediate Similarity	NPC228700
0.8065	Intermediate Similarity	NPC236459
0.8046	Intermediate Similarity	NPC143250
0.8043	Intermediate Similarity	NPC83242
0.8041	Intermediate Similarity	NPC477264
0.8022	Intermediate Similarity	NPC237938
0.8022	Intermediate Similarity	NPC181871
0.8022	Intermediate Similarity	NPC475689
0.8022	Intermediate Similarity	NPC219535
0.8022	Intermediate Similarity	NPC9060
0.7961	Intermediate Similarity	NPC153587
0.7959	Intermediate Similarity	NPC266417
0.7957	Intermediate Similarity	NPC470920
0.7938	Intermediate Similarity	NPC62407
0.7938	Intermediate Similarity	NPC287354
0.7935	Intermediate Similarity	NPC474572
0.7885	Intermediate Similarity	NPC204652
0.7885	Intermediate Similarity	NPC16657
0.7872	Intermediate Similarity	NPC476379
0.7872	Intermediate Similarity	NPC221993
0.7872	Intermediate Similarity	NPC471221
0.7849	Intermediate Similarity	NPC120395
0.7849	Intermediate Similarity	NPC476717
0.7849	Intermediate Similarity	NPC248216
0.7826	Intermediate Similarity	NPC473299
0.7778	Intermediate Similarity	NPC134227
0.7778	Intermediate Similarity	NPC475490
0.7755	Intermediate Similarity	NPC470031
0.7742	Intermediate Similarity	NPC477445
0.7742	Intermediate Similarity	NPC477205
0.7736	Intermediate Similarity	NPC473062
0.7732	Intermediate Similarity	NPC476189
0.7723	Intermediate Similarity	NPC178853
0.7714	Intermediate Similarity	NPC227879
0.7714	Intermediate Similarity	NPC208333
0.7708	Intermediate Similarity	NPC472146
0.7708	Intermediate Similarity	NPC475211
0.7708	Intermediate Similarity	NPC77756
0.7708	Intermediate Similarity	NPC88337
0.7708	Intermediate Similarity	NPC185529
0.7706	Intermediate Similarity	NPC146432
0.7706	Intermediate Similarity	NPC470778
0.7701	Intermediate Similarity	NPC55508
0.7692	Intermediate Similarity	NPC203974
0.7685	Intermediate Similarity	NPC470115
0.7685	Intermediate Similarity	NPC470116
0.7684	Intermediate Similarity	NPC477614
0.7684	Intermediate Similarity	NPC131104
0.7684	Intermediate Similarity	NPC473319
0.7684	Intermediate Similarity	NPC3032
0.7684	Intermediate Similarity	NPC226491
0.7684	Intermediate Similarity	NPC476435
0.7677	Intermediate Similarity	NPC476728
0.7677	Intermediate Similarity	NPC116683
0.7674	Intermediate Similarity	NPC96322
0.7667	Intermediate Similarity	NPC275243
0.7647	Intermediate Similarity	NPC470172
0.7647	Intermediate Similarity	NPC471254
0.7642	Intermediate Similarity	NPC470622
0.7634	Intermediate Similarity	NPC105895
0.7634	Intermediate Similarity	NPC471044
0.7634	Intermediate Similarity	NPC473336
0.7629	Intermediate Similarity	NPC476934
0.7615	Intermediate Similarity	NPC16081
0.7615	Intermediate Similarity	NPC173686
0.7615	Intermediate Similarity	NPC89929
0.7609	Intermediate Similarity	NPC13494
0.7604	Intermediate Similarity	NPC24705
0.7604	Intermediate Similarity	NPC61688
0.7604	Intermediate Similarity	NPC56962
0.7604	Intermediate Similarity	NPC200580
0.76	Intermediate Similarity	NPC472273
0.76	Intermediate Similarity	NPC74466
0.76	Intermediate Similarity	NPC470632
0.7596	Intermediate Similarity	NPC470587
0.7593	Intermediate Similarity	NPC97002
0.7586	Intermediate Similarity	NPC474755
0.7582	Intermediate Similarity	NPC472951
0.7582	Intermediate Similarity	NPC472943
0.7576	Intermediate Similarity	NPC305808
0.7576	Intermediate Similarity	NPC217329
0.7576	Intermediate Similarity	NPC17336
0.7573	Intermediate Similarity	NPC471253
0.7573	Intermediate Similarity	NPC473406
0.7573	Intermediate Similarity	NPC34562
0.7551	Intermediate Similarity	NPC472148
0.7551	Intermediate Similarity	NPC472147
0.7547	Intermediate Similarity	NPC236753
0.7547	Intermediate Similarity	NPC228190
0.7545	Intermediate Similarity	NPC179429
0.7528	Intermediate Similarity	NPC471046
0.7527	Intermediate Similarity	NPC269684
0.7526	Intermediate Similarity	NPC18536
0.7526	Intermediate Similarity	NPC470114
0.7526	Intermediate Similarity	NPC50443
0.7525	Intermediate Similarity	NPC476294
0.7525	Intermediate Similarity	NPC472144
0.7525	Intermediate Similarity	NPC253995
0.7523	Intermediate Similarity	NPC323821
0.7523	Intermediate Similarity	NPC143268
0.7523	Intermediate Similarity	NPC477465
0.7523	Intermediate Similarity	NPC268238
0.7523	Intermediate Similarity	NPC45218
0.75	Intermediate Similarity	NPC88469
0.75	Intermediate Similarity	NPC193785
0.75	Intermediate Similarity	NPC475785
0.75	Intermediate Similarity	NPC475765
0.7477	Intermediate Similarity	NPC100908
0.7477	Intermediate Similarity	NPC297179
0.7476	Intermediate Similarity	NPC80640
0.7475	Intermediate Similarity	NPC206878
0.7474	Intermediate Similarity	NPC80700
0.7474	Intermediate Similarity	NPC302111
0.7474	Intermediate Similarity	NPC474008
0.7474	Intermediate Similarity	NPC474215
0.7474	Intermediate Similarity	NPC475729
0.7473	Intermediate Similarity	NPC73013
0.7473	Intermediate Similarity	NPC477287
0.7455	Intermediate Similarity	NPC213084
0.7455	Intermediate Similarity	NPC190185
0.7453	Intermediate Similarity	NPC469826
0.7453	Intermediate Similarity	NPC472079
0.7453	Intermediate Similarity	NPC289702
0.7453	Intermediate Similarity	NPC208461
0.7451	Intermediate Similarity	NPC80417
0.7449	Intermediate Similarity	NPC470230
0.7449	Intermediate Similarity	NPC475878
0.7449	Intermediate Similarity	NPC52756
0.7447	Intermediate Similarity	NPC34984
0.7447	Intermediate Similarity	NPC50438
0.7447	Intermediate Similarity	NPC25037
0.7447	Intermediate Similarity	NPC319909
0.7444	Intermediate Similarity	NPC471151
0.7434	Intermediate Similarity	NPC470779
0.7431	Intermediate Similarity	NPC33360
0.7431	Intermediate Similarity	NPC94509
0.7426	Intermediate Similarity	NPC472145
0.7426	Intermediate Similarity	NPC469810
0.7426	Intermediate Similarity	NPC471241
0.7419	Intermediate Similarity	NPC271163
0.7419	Intermediate Similarity	NPC477284
0.7407	Intermediate Similarity	NPC157476
0.7404	Intermediate Similarity	NPC469985
0.7396	Intermediate Similarity	NPC263802
0.7396	Intermediate Similarity	NPC202937
0.7391	Intermediate Similarity	NPC1882
0.7386	Intermediate Similarity	NPC109510
0.7386	Intermediate Similarity	NPC123122
0.7383	Intermediate Similarity	NPC87393
0.7374	Intermediate Similarity	NPC469315
0.7368	Intermediate Similarity	NPC473350
0.7368	Intermediate Similarity	NPC131350
0.7368	Intermediate Similarity	NPC476715
0.7364	Intermediate Similarity	NPC299849
0.7364	Intermediate Similarity	NPC473798
0.7358	Intermediate Similarity	NPC201908
0.7358	Intermediate Similarity	NPC126753
0.7358	Intermediate Similarity	NPC176949
0.7353	Intermediate Similarity	NPC474793
0.7353	Intermediate Similarity	NPC474724
0.734	Intermediate Similarity	NPC15091
0.7339	Intermediate Similarity	NPC157571
0.7339	Intermediate Similarity	NPC477489
0.7339	Intermediate Similarity	NPC476964
0.7333	Intermediate Similarity	NPC327093
0.7333	Intermediate Similarity	NPC474020
0.7333	Intermediate Similarity	NPC267637
0.7321	Intermediate Similarity	NPC17772
0.732	Intermediate Similarity	NPC56777
0.732	Intermediate Similarity	NPC201607
0.7315	Intermediate Similarity	NPC66513
0.7312	Intermediate Similarity	NPC476071
0.7308	Intermediate Similarity	NPC244969
0.7308	Intermediate Similarity	NPC213528
0.73	Intermediate Similarity	NPC470424
0.73	Intermediate Similarity	NPC470423
0.7297	Intermediate Similarity	NPC96312
0.7297	Intermediate Similarity	NPC251236

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 NPC474379 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	526
0.1-0.2	3966
0.2-0.3	3081
0.3-0.4	968
0.4-0.5	292
0.5-0.6	213
0.6-0.7	98
0.7-0.8	6
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
0.7549	Intermediate Similarity	NPD1700	Approved
0.7453	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD6115	Approved
0.6989	Remote Similarity	NPD6697	Approved
0.6989	Remote Similarity	NPD6118	Approved
0.6989	Remote Similarity	NPD6114	Approved
0.6917	Remote Similarity	NPD7736	Approved
0.6889	Remote Similarity	NPD5777	Approved
0.6882	Remote Similarity	NPD6116	Phase 1
0.6864	Remote Similarity	NPD8328	Phase 3
0.6848	Remote Similarity	NPD3703	Phase 2
0.6807	Remote Similarity	NPD7492	Approved
0.6789	Remote Similarity	NPD6008	Approved
0.6774	Remote Similarity	NPD6117	Approved
0.6771	Remote Similarity	NPD1780	Approved
0.6771	Remote Similarity	NPD1779	Approved
0.6752	Remote Similarity	NPD6319	Approved
0.6752	Remote Similarity	NPD6059	Approved
0.6752	Remote Similarity	NPD6054	Approved
0.675	Remote Similarity	NPD6616	Approved
0.6695	Remote Similarity	NPD6921	Approved
0.6694	Remote Similarity	NPD7078	Approved
0.6694	Remote Similarity	NPD8293	Discontinued
0.6639	Remote Similarity	NPD6370	Approved
0.6636	Remote Similarity	NPD6402	Approved
0.6636	Remote Similarity	NPD5739	Approved
0.6636	Remote Similarity	NPD7128	Approved
0.6636	Remote Similarity	NPD6675	Approved
0.6579	Remote Similarity	NPD8297	Approved
0.6577	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6555	Remote Similarity	NPD6016	Approved
0.6555	Remote Similarity	NPD6015	Approved
0.6518	Remote Similarity	NPD7320	Approved
0.6518	Remote Similarity	NPD6881	Approved
0.6518	Remote Similarity	NPD6899	Approved
0.65	Remote Similarity	NPD5988	Approved
0.6489	Remote Similarity	NPD3702	Approved
0.646	Remote Similarity	NPD6372	Approved
0.646	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.646	Remote Similarity	NPD6373	Approved
0.646	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6446	Remote Similarity	NPD7604	Phase 2
0.6442	Remote Similarity	NPD8035	Phase 2
0.6442	Remote Similarity	NPD8034	Phase 2
0.6429	Remote Similarity	NPD5701	Approved
0.6429	Remote Similarity	NPD5697	Approved
0.6404	Remote Similarity	NPD7102	Approved
0.6404	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD6883	Approved
0.6404	Remote Similarity	NPD7290	Approved
0.6379	Remote Similarity	NPD8133	Approved
0.6379	Remote Similarity	NPD4632	Approved
0.6364	Remote Similarity	NPD8301	Approved
0.6364	Remote Similarity	NPD8300	Approved
0.6356	Remote Similarity	NPD6009	Approved
0.6348	Remote Similarity	NPD6847	Approved
0.6348	Remote Similarity	NPD6649	Approved
0.6348	Remote Similarity	NPD6869	Approved
0.6348	Remote Similarity	NPD6617	Approved
0.6348	Remote Similarity	NPD8130	Phase 1
0.6348	Remote Similarity	NPD6650	Approved
0.6344	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6344	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD7900	Approved
0.632	Remote Similarity	NPD7319	Approved
0.6316	Remote Similarity	NPD6012	Approved
0.6316	Remote Similarity	NPD6013	Approved
0.6316	Remote Similarity	NPD6014	Approved
0.6304	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6304	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6293	Remote Similarity	NPD6882	Approved
0.6281	Remote Similarity	NPD5983	Phase 2
0.624	Remote Similarity	NPD6033	Approved
0.6237	Remote Similarity	NPD4789	Approved
0.6228	Remote Similarity	NPD6011	Approved
0.6218	Remote Similarity	NPD7115	Discovery
0.6214	Remote Similarity	NPD3573	Approved
0.621	Remote Similarity	NPD7507	Approved
0.621	Remote Similarity	NPD6336	Discontinued
0.6207	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6196	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6196	Remote Similarity	NPD5360	Phase 3
0.6196	Remote Similarity	NPD229	Approved
0.6176	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.617	Remote Similarity	NPD6081	Approved
0.6168	Remote Similarity	NPD7748	Approved
0.6162	Remote Similarity	NPD6928	Phase 2
0.6154	Remote Similarity	NPD5737	Approved
0.6154	Remote Similarity	NPD4224	Phase 2
0.6154	Remote Similarity	NPD6672	Approved
0.6147	Remote Similarity	NPD7902	Approved
0.6139	Remote Similarity	NPD3669	Approved
0.6139	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6134	Remote Similarity	NPD6940	Discontinued
0.6121	Remote Similarity	NPD4634	Approved
0.6075	Remote Similarity	NPD8171	Discontinued
0.6064	Remote Similarity	NPD4245	Approved
0.6064	Remote Similarity	NPD4244	Approved
0.6	Remote Similarity	NPD6412	Phase 2
0.6	Remote Similarity	NPD6274	Approved
0.6	Remote Similarity	NPD6083	Phase 2
0.6	Remote Similarity	NPD6084	Phase 2
0.6	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6	Remote Similarity	NPD4755	Approved
0.5984	Remote Similarity	NPD7101	Approved
0.5984	Remote Similarity	NPD7100	Approved
0.5981	Remote Similarity	NPD7515	Phase 2
0.5965	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.5965	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.5963	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5962	Remote Similarity	NPD6098	Approved
0.5957	Remote Similarity	NPD3698	Phase 2
0.5957	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.5946	Remote Similarity	NPD7638	Approved
0.5943	Remote Similarity	NPD6904	Approved
0.5943	Remote Similarity	NPD6080	Approved
0.5943	Remote Similarity	NPD6673	Approved
0.5926	Remote Similarity	NPD6399	Phase 3
0.5902	Remote Similarity	NPD6335	Approved
0.5895	Remote Similarity	NPD2687	Approved
0.5895	Remote Similarity	NPD2254	Approved
0.5895	Remote Similarity	NPD2686	Approved
0.5893	Remote Similarity	NPD7640	Approved
0.5893	Remote Similarity	NPD4696	Approved
0.5893	Remote Similarity	NPD5285	Approved
0.5893	Remote Similarity	NPD5286	Approved
0.5893	Remote Similarity	NPD4700	Approved
0.5893	Remote Similarity	NPD7639	Approved
0.5887	Remote Similarity	NPD6909	Approved
0.5887	Remote Similarity	NPD6908	Approved
0.587	Remote Similarity	NPD9496	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD6411	Approved
0.5833	Remote Similarity	NPD4758	Discontinued
0.582	Remote Similarity	NPD6317	Approved
0.5818	Remote Similarity	NPD5695	Phase 3
0.5812	Remote Similarity	NPD6686	Approved
0.581	Remote Similarity	NPD7334	Approved
0.581	Remote Similarity	NPD6684	Approved
0.581	Remote Similarity	NPD5330	Approved
0.581	Remote Similarity	NPD7146	Approved
0.581	Remote Similarity	NPD6409	Approved
0.581	Remote Similarity	NPD7521	Approved
0.5804	Remote Similarity	NPD5696	Approved
0.58	Remote Similarity	NPD5364	Discontinued
0.58	Remote Similarity	NPD3671	Phase 1
0.58	Remote Similarity	NPD4238	Approved
0.58	Remote Similarity	NPD4802	Phase 2
0.5789	Remote Similarity	NPD5224	Approved
0.5789	Remote Similarity	NPD4633	Approved
0.5789	Remote Similarity	NPD5225	Approved
0.5789	Remote Similarity	NPD5211	Phase 2
0.5789	Remote Similarity	NPD5226	Approved
0.5789	Remote Similarity	NPD7632	Discontinued
0.5772	Remote Similarity	NPD6313	Approved
0.5772	Remote Similarity	NPD6314	Approved
0.576	Remote Similarity	NPD8517	Approved
0.576	Remote Similarity	NPD8516	Approved
0.576	Remote Similarity	NPD8515	Approved
0.576	Remote Similarity	NPD8513	Phase 3
0.5752	Remote Similarity	NPD8418	Phase 2
0.5739	Remote Similarity	NPD5175	Approved
0.5739	Remote Similarity	NPD5174	Approved
0.5738	Remote Similarity	NPD6868	Approved
0.5727	Remote Similarity	NPD5282	Discontinued
0.5702	Remote Similarity	NPD5223	Approved
0.5701	Remote Similarity	NPD6903	Approved
0.5699	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.569	Remote Similarity	NPD5141	Approved
0.5688	Remote Similarity	NPD5693	Phase 1
0.5688	Remote Similarity	NPD6050	Approved
0.5664	Remote Similarity	NPD4225	Approved
0.5652	Remote Similarity	NPD8085	Approved
0.5652	Remote Similarity	NPD8086	Approved
0.5652	Remote Similarity	NPD8138	Approved
0.5652	Remote Similarity	NPD8083	Approved
0.5652	Remote Similarity	NPD8082	Approved
0.5652	Remote Similarity	NPD8084	Approved
0.5652	Remote Similarity	NPD8139	Approved
0.5648	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5648	Remote Similarity	NPD5328	Approved
0.5648	Remote Similarity	NPD6101	Approved
0.5645	Remote Similarity	NPD7328	Approved
0.5645	Remote Similarity	NPD7327	Approved
0.5641	Remote Similarity	NPD4768	Approved
0.5641	Remote Similarity	NPD4767	Approved
0.5635	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.5625	Remote Similarity	NPD5222	Approved
0.5625	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5625	Remote Similarity	NPD4697	Phase 3
0.5625	Remote Similarity	NPD5221	Approved
0.5603	Remote Similarity	NPD8275	Approved
0.5603	Remote Similarity	NPD8276	Approved
0.5603	Remote Similarity	NPD4754	Approved
0.56	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