NPASS Compound

Structure

NPC469437 OpenBabel07101718242D 30 34 0 0 1 0 0 0 0 0999 V2000 -1.5880 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7357 0.3438 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3854 -0.9960 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5320 -0.6611 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1023 -0.4244 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3953 0.2455 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9656 0.4822 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7940 1.3753 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3821 -1.3753 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3821 1.3753 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3821 0.0788 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7940 0.4584 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1121 0.8172 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5880 -0.9169 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 1.8337 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5880 1.8337 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3821 0.4584 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7453 -0.2278 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.1761 -0.9169 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5880 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7940 1.3753 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7940 0.4584 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9755 1.7238 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0188 -0.2278 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.7506 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5880 2.7506 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6923 2.2955 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 3.1761 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1220 2.0588 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 12 1 0 0 0 0 2 24 1 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 7 2 0 0 0 0 6 13 2 0 0 0 0 7 13 1 0 0 0 0 8 12 2 0 0 0 0 8 15 1 0 0 0 0 10 16 2 0 0 0 0 10 17 1 0 0 0 0 11 18 1 0 0 0 0 11 24 1 0 0 0 0 12 28 1 0 0 0 0 13 23 1 0 0 0 0 14 9 1 1 0 0 0 14 18 1 0 0 0 0 14 20 1 0 0 0 0 15 21 1 0 0 0 0 15 25 2 0 0 0 0 16 21 1 0 0 0 0 16 26 1 0 0 0 0 17 20 2 0 0 0 0 17 29 1 0 0 0 0 18 30 1 6 0 0 0 19 9 1 1 0 0 0 19 24 1 0 0 0 0 19 29 1 0 0 0 0 20 22 1 0 0 0 0 21 22 2 0 0 0 0 22 28 1 0 0 0 0 23 27 2 0 0 0 0 23 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	407.14
Volume:	403.592
LogP:	3.929
LogD:	3.106
LogS:	-4.04
# Rotatable Bonds:	3
TPSA:	89.21
# H-Bond Aceptor:	7
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.653
Synthetic Accessibility Score:	4.59
Fsp3:	0.304
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:	-4.882
MDCK Permeability:	6.285472773015499e-05
Pgp-inhibitor:	0.026
Pgp-substrate:	0.016
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.388

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.788
Plasma Protein Binding (PPB):	87.39446258544922%
Volume Distribution (VD):	1.361
Pgp-substrate:	11.607780456542969%

ADMET: Metabolism

CYP1A2-inhibitor:	0.296
CYP1A2-substrate:	0.24
CYP2C19-inhibitor:	0.139
CYP2C19-substrate:	0.837
CYP2C9-inhibitor:	0.418
CYP2C9-substrate:	0.918
CYP2D6-inhibitor:	0.93
CYP2D6-substrate:	0.462
CYP3A4-inhibitor:	0.458
CYP3A4-substrate:	0.705

ADMET: Excretion

Clearance (CL):	10.566
Half-life (T1/2):	0.509

ADMET: Toxicity

hERG Blockers:	0.294
Human Hepatotoxicity (H-HT):	0.646
Drug-inuced Liver Injury (DILI):	0.968
AMES Toxicity:	0.355
Rat Oral Acute Toxicity:	0.345
Maximum Recommended Daily Dose:	0.89
Skin Sensitization:	0.828
Carcinogencity:	0.821
Eye Corrosion:	0.003
Eye Irritation:	0.016
Respiratory Toxicity:	0.872

Download Data

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

Natural Product: NPC469437

Natural Product ID:	NPC469437
*Common Name:**	Chrotacumine A
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	PJWARXSHHFSDKD-ZMYBRWDISA-N
Standard InCHI:	InChI=1S/C23H21NO6/c1-12-8-15(25)21-16(26)10-17-20(22(21)28-12)14-9-19(29-17)24(2)11-18(14)30-23(27)13-6-4-3-5-7-13/h3-8,10,14,18-19,26H,9,11H2,1-2H3/t14-,18-,19+/m1/s1
SMILES:	CN1C[C@@H](OC(=O)c2ccccc2)[C@H]2C[C@@H]1Oc1c2c2oc(C)cc(=O)c2c(c1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1078718
PubChem CID:	46882760
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0003543] Pyranochromenes

*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
NPO654	Dysoxylum acutangulum	Species	Meliaceae	Eukaryota	n.a.	alkaloids	n.a.	PMID[19757855]
NPO654	Dysoxylum acutangulum	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO654	Dysoxylum acutangulum	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
IC50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	10000.0	nM	PMID[464843]

☑ 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 NPC469437 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	296
0.1-0.2	1304
0.2-0.3	4095
0.3-0.4	10492
0.4-0.5	7575
0.5-0.6	7137
0.6-0.7	6746
0.7-0.8	4963
0.8-0.85	82
0.85-0.9	1
0.9-0.95	4
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9583	High Similarity	NPC309692
0.927	High Similarity	NPC83019
0.9231	High Similarity	NPC129578
0.9213	High Similarity	NPC204580
0.8889	High Similarity	NPC264938
0.8462	Intermediate Similarity	NPC209142
0.8462	Intermediate Similarity	NPC312549
0.8391	Intermediate Similarity	NPC97812
0.8391	Intermediate Similarity	NPC175513
0.838	Intermediate Similarity	NPC327005
0.8353	Intermediate Similarity	NPC78835
0.8353	Intermediate Similarity	NPC309512
0.8353	Intermediate Similarity	NPC204561
0.8353	Intermediate Similarity	NPC316960
0.8353	Intermediate Similarity	NPC317715
0.8353	Intermediate Similarity	NPC148945
0.8343	Intermediate Similarity	NPC104236
0.8343	Intermediate Similarity	NPC473016
0.8343	Intermediate Similarity	NPC19238
0.8343	Intermediate Similarity	NPC164205
0.8294	Intermediate Similarity	NPC471115
0.8294	Intermediate Similarity	NPC29777
0.8294	Intermediate Similarity	NPC474735
0.8284	Intermediate Similarity	NPC39195
0.8246	Intermediate Similarity	NPC290671
0.8229	Intermediate Similarity	NPC314946
0.8225	Intermediate Similarity	NPC23728
0.8225	Intermediate Similarity	NPC296998
0.8225	Intermediate Similarity	NPC473077
0.8225	Intermediate Similarity	NPC110303
0.8225	Intermediate Similarity	NPC308200
0.8218	Intermediate Similarity	NPC475184
0.8214	Intermediate Similarity	NPC271288
0.8214	Intermediate Similarity	NPC473013
0.8214	Intermediate Similarity	NPC473015
0.8187	Intermediate Similarity	NPC180351
0.8187	Intermediate Similarity	NPC472633
0.8182	Intermediate Similarity	NPC114652
0.8176	Intermediate Similarity	NPC160821
0.8176	Intermediate Similarity	NPC168085
0.8176	Intermediate Similarity	NPC132592
0.8176	Intermediate Similarity	NPC161191
0.8176	Intermediate Similarity	NPC145467
0.8166	Intermediate Similarity	NPC54577
0.8166	Intermediate Similarity	NPC67805
0.8166	Intermediate Similarity	NPC142405
0.8166	Intermediate Similarity	NPC176229
0.8166	Intermediate Similarity	NPC470647
0.8166	Intermediate Similarity	NPC476088
0.8166	Intermediate Similarity	NPC195621
0.8166	Intermediate Similarity	NPC154217
0.8166	Intermediate Similarity	NPC472629
0.8166	Intermediate Similarity	NPC470322
0.8166	Intermediate Similarity	NPC88964
0.8166	Intermediate Similarity	NPC214774
0.8166	Intermediate Similarity	NPC312973
0.8166	Intermediate Similarity	NPC267375
0.8166	Intermediate Similarity	NPC111786
0.8166	Intermediate Similarity	NPC301276
0.8166	Intermediate Similarity	NPC474161
0.8166	Intermediate Similarity	NPC475052
0.8166	Intermediate Similarity	NPC20488
0.8166	Intermediate Similarity	NPC246948
0.8166	Intermediate Similarity	NPC83357
0.8166	Intermediate Similarity	NPC299011
0.8166	Intermediate Similarity	NPC477955
0.8161	Intermediate Similarity	NPC69531
0.8161	Intermediate Similarity	NPC32867
0.8155	Intermediate Similarity	NPC68104
0.8155	Intermediate Similarity	NPC39329
0.8155	Intermediate Similarity	NPC85162
0.8155	Intermediate Similarity	NPC81697
0.8155	Intermediate Similarity	NPC221432
0.8155	Intermediate Similarity	NPC77794
0.8155	Intermediate Similarity	NPC278249
0.8155	Intermediate Similarity	NPC223812
0.8155	Intermediate Similarity	NPC257097
0.8155	Intermediate Similarity	NPC150408
0.8155	Intermediate Similarity	NPC149026
0.8155	Intermediate Similarity	NPC143896
0.8155	Intermediate Similarity	NPC164980
0.8155	Intermediate Similarity	NPC175504
0.8155	Intermediate Similarity	NPC125894
0.8155	Intermediate Similarity	NPC310130
0.8155	Intermediate Similarity	NPC107177
0.8155	Intermediate Similarity	NPC169591
0.8155	Intermediate Similarity	NPC91560
0.8155	Intermediate Similarity	NPC75049
0.815	Intermediate Similarity	NPC109594
0.815	Intermediate Similarity	NPC223701
0.815	Intermediate Similarity	NPC472583
0.815	Intermediate Similarity	NPC112701
0.815	Intermediate Similarity	NPC326592
0.815	Intermediate Similarity	NPC7989
0.814	Intermediate Similarity	NPC178484
0.814	Intermediate Similarity	NPC325429
0.8136	Intermediate Similarity	NPC473022
0.8129	Intermediate Similarity	NPC471114
0.8129	Intermediate Similarity	NPC5173
0.8129	Intermediate Similarity	NPC317492
0.8125	Intermediate Similarity	NPC98023
0.8125	Intermediate Similarity	NPC114147
0.8125	Intermediate Similarity	NPC226462
0.8118	Intermediate Similarity	NPC237635
0.8118	Intermediate Similarity	NPC79469
0.8118	Intermediate Similarity	NPC10990
0.8118	Intermediate Similarity	NPC104406
0.8118	Intermediate Similarity	NPC24673
0.8118	Intermediate Similarity	NPC283234
0.8118	Intermediate Similarity	NPC201731
0.8118	Intermediate Similarity	NPC140120
0.8118	Intermediate Similarity	NPC97716
0.8118	Intermediate Similarity	NPC300988
0.8114	Intermediate Similarity	NPC322459
0.8114	Intermediate Similarity	NPC1796
0.8114	Intermediate Similarity	NPC318527
0.8114	Intermediate Similarity	NPC323627
0.8114	Intermediate Similarity	NPC324358
0.8107	Intermediate Similarity	NPC131568
0.8107	Intermediate Similarity	NPC124780
0.8107	Intermediate Similarity	NPC224714
0.8107	Intermediate Similarity	NPC196137
0.8107	Intermediate Similarity	NPC470890
0.8107	Intermediate Similarity	NPC1886
0.8107	Intermediate Similarity	NPC303185
0.8107	Intermediate Similarity	NPC319752
0.8107	Intermediate Similarity	NPC469953
0.8107	Intermediate Similarity	NPC184649
0.8107	Intermediate Similarity	NPC197252
0.8107	Intermediate Similarity	NPC131579
0.8107	Intermediate Similarity	NPC311144
0.8107	Intermediate Similarity	NPC473014
0.8107	Intermediate Similarity	NPC236766
0.8107	Intermediate Similarity	NPC87486
0.8107	Intermediate Similarity	NPC209040
0.8107	Intermediate Similarity	NPC235217
0.8103	Intermediate Similarity	NPC66441
0.8103	Intermediate Similarity	NPC300668
0.8103	Intermediate Similarity	NPC134171
0.8103	Intermediate Similarity	NPC182555
0.8103	Intermediate Similarity	NPC477958
0.8095	Intermediate Similarity	NPC107572
0.8095	Intermediate Similarity	NPC228504
0.8095	Intermediate Similarity	NPC177354
0.8095	Intermediate Similarity	NPC167624
0.8095	Intermediate Similarity	NPC202981
0.8095	Intermediate Similarity	NPC148757
0.8095	Intermediate Similarity	NPC10937
0.8095	Intermediate Similarity	NPC166934
0.8095	Intermediate Similarity	NPC166482
0.8095	Intermediate Similarity	NPC324134
0.8095	Intermediate Similarity	NPC64915
0.8095	Intermediate Similarity	NPC324436
0.8095	Intermediate Similarity	NPC265040
0.8095	Intermediate Similarity	NPC328164
0.8095	Intermediate Similarity	NPC76372
0.8095	Intermediate Similarity	NPC161506
0.8095	Intermediate Similarity	NPC37496
0.8095	Intermediate Similarity	NPC40833
0.8095	Intermediate Similarity	NPC194432
0.8095	Intermediate Similarity	NPC182852
0.8095	Intermediate Similarity	NPC76338
0.8095	Intermediate Similarity	NPC296917
0.8095	Intermediate Similarity	NPC306829
0.8095	Intermediate Similarity	NPC32739
0.8095	Intermediate Similarity	NPC78
0.8095	Intermediate Similarity	NPC227579
0.8095	Intermediate Similarity	NPC1089
0.8095	Intermediate Similarity	NPC125855
0.8095	Intermediate Similarity	NPC220998
0.8095	Intermediate Similarity	NPC223500
0.8095	Intermediate Similarity	NPC66515
0.8092	Intermediate Similarity	NPC256141
0.8092	Intermediate Similarity	NPC475790
0.8092	Intermediate Similarity	NPC244583
0.8092	Intermediate Similarity	NPC56232
0.8092	Intermediate Similarity	NPC10807
0.8092	Intermediate Similarity	NPC166067
0.8092	Intermediate Similarity	NPC150123
0.8092	Intermediate Similarity	NPC161881
0.8081	Intermediate Similarity	NPC61258
0.8081	Intermediate Similarity	NPC321896
0.8081	Intermediate Similarity	NPC476185
0.8079	Intermediate Similarity	NPC92589
0.807	Intermediate Similarity	NPC266572
0.807	Intermediate Similarity	NPC161864
0.807	Intermediate Similarity	NPC296869
0.807	Intermediate Similarity	NPC6511
0.807	Intermediate Similarity	NPC208303
0.807	Intermediate Similarity	NPC321623
0.807	Intermediate Similarity	NPC189087
0.8068	Intermediate Similarity	NPC51760
0.8068	Intermediate Similarity	NPC295090
0.8068	Intermediate Similarity	NPC105584
0.8068	Intermediate Similarity	NPC15815
0.8068	Intermediate Similarity	NPC51247
0.8059	Intermediate Similarity	NPC470133
0.8059	Intermediate Similarity	NPC285630
0.8059	Intermediate Similarity	NPC290133
0.8059	Intermediate Similarity	NPC127059

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 NPC469437 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	201
0.1-0.2	664
0.2-0.3	1294
0.3-0.4	2225
0.4-0.5	2416
0.5-0.6	1569
0.6-0.7	610
0.7-0.8	163
0.8-0.85	5
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8889	High Similarity	NPD4360	Phase 2
0.8889	High Similarity	NPD4363	Phase 3
0.8857	High Similarity	NPD4419	Clinical (unspecified phase)
0.8353	Intermediate Similarity	NPD5890	Approved
0.8353	Intermediate Similarity	NPD5889	Approved
0.8333	Intermediate Similarity	NPD4361	Phase 2
0.8333	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.8187	Intermediate Similarity	NPD6585	Discontinued
0.8158	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.8136	Intermediate Similarity	NPD5710	Approved
0.8136	Intermediate Similarity	NPD5711	Approved
0.8035	Intermediate Similarity	NPD7411	Suspended
0.8011	Intermediate Similarity	NPD7075	Discontinued
0.8	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7977	Intermediate Similarity	NPD4380	Phase 2
0.7944	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7943	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7943	Intermediate Similarity	NPD7819	Suspended
0.7941	Intermediate Similarity	NPD7213	Phase 3
0.7941	Intermediate Similarity	NPD7212	Phase 2
0.7895	Intermediate Similarity	NPD7447	Phase 1
0.7857	Intermediate Similarity	NPD1549	Phase 2
0.7841	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7816	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7814	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7809	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7798	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7798	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD6844	Discontinued
0.7784	Intermediate Similarity	NPD6801	Discontinued
0.7778	Intermediate Similarity	NPD6959	Discontinued
0.7778	Intermediate Similarity	NPD7701	Phase 2
0.776	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7753	Intermediate Similarity	NPD7768	Phase 2
0.7738	Intermediate Similarity	NPD2796	Approved
0.7732	Intermediate Similarity	NPD8285	Discontinued
0.7727	Intermediate Similarity	NPD7584	Approved
0.7688	Intermediate Similarity	NPD7585	Approved
0.7684	Intermediate Similarity	NPD7577	Discontinued
0.7679	Intermediate Similarity	NPD1510	Phase 2
0.7663	Intermediate Similarity	NPD7177	Discontinued
0.7661	Intermediate Similarity	NPD3750	Approved
0.7647	Intermediate Similarity	NPD7549	Discontinued
0.7641	Intermediate Similarity	NPD7810	Phase 3
0.7641	Intermediate Similarity	NPD7811	Phase 3
0.7638	Intermediate Similarity	NPD7583	Approved
0.7626	Intermediate Similarity	NPD8319	Approved
0.7626	Intermediate Similarity	NPD8320	Phase 1
0.7624	Intermediate Similarity	NPD5494	Approved
0.7616	Intermediate Similarity	NPD3295	Clinical (unspecified phase)
0.7609	Intermediate Similarity	NPD3446	Phase 1
0.76	Intermediate Similarity	NPD7427	Discontinued
0.7598	Intermediate Similarity	NPD5353	Approved
0.7584	Intermediate Similarity	NPD1934	Approved
0.7572	Intermediate Similarity	NPD6667	Approved
0.7572	Intermediate Similarity	NPD6666	Approved
0.7554	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7554	Intermediate Similarity	NPD6166	Phase 2
0.7554	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7554	Intermediate Similarity	NPD3451	Clinical (unspecified phase)
0.7541	Intermediate Similarity	NPD6808	Phase 2
0.7529	Intermediate Similarity	NPD6799	Approved
0.7528	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7527	Intermediate Similarity	NPD7054	Approved
0.7525	Intermediate Similarity	NPD5006	Approved
0.7525	Intermediate Similarity	NPD5005	Approved
0.7514	Intermediate Similarity	NPD3749	Approved
0.75	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5242	Approved
0.75	Intermediate Similarity	NPD2654	Approved
0.7488	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7488	Intermediate Similarity	NPD7783	Phase 2
0.7487	Intermediate Similarity	NPD7074	Phase 3
0.7487	Intermediate Similarity	NPD7472	Approved
0.7472	Intermediate Similarity	NPD6599	Discontinued
0.7459	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD6797	Phase 2
0.7442	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD1240	Approved
0.7433	Intermediate Similarity	NPD5844	Phase 1
0.7418	Intermediate Similarity	NPD8005	Clinical (unspecified phase)
0.7411	Intermediate Similarity	NPD4420	Approved
0.7407	Intermediate Similarity	NPD7251	Discontinued
0.7403	Intermediate Similarity	NPD3817	Phase 2
0.7401	Intermediate Similarity	NPD5403	Approved
0.7401	Intermediate Similarity	NPD920	Approved
0.74	Intermediate Similarity	NPD7064	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD4622	Approved
0.7396	Intermediate Similarity	NPD4618	Approved
0.7389	Intermediate Similarity	NPD8151	Discontinued
0.738	Intermediate Similarity	NPD5940	Clinical (unspecified phase)
0.7376	Intermediate Similarity	NPD6973	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD2799	Discontinued
0.7368	Intermediate Similarity	NPD7808	Phase 3
0.7368	Intermediate Similarity	NPD3748	Approved
0.7363	Intermediate Similarity	NPD5019	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD1607	Approved
0.7348	Intermediate Similarity	NPD2801	Approved
0.734	Intermediate Similarity	NPD6020	Phase 2
0.7337	Intermediate Similarity	NPD3140	Approved
0.7337	Intermediate Similarity	NPD3142	Approved
0.733	Intermediate Similarity	NPD1511	Approved
0.7326	Intermediate Similarity	NPD4477	Approved
0.7326	Intermediate Similarity	NPD2935	Discontinued
0.7326	Intermediate Similarity	NPD4476	Approved
0.7326	Intermediate Similarity	NPD1551	Phase 2
0.7326	Intermediate Similarity	NPD7473	Discontinued
0.7316	Intermediate Similarity	NPD6559	Discontinued
0.7316	Intermediate Similarity	NPD7038	Approved
0.7316	Intermediate Similarity	NPD7039	Approved
0.7313	Intermediate Similarity	NPD7696	Phase 3
0.7313	Intermediate Similarity	NPD7497	Discontinued
0.7313	Intermediate Similarity	NPD7697	Approved
0.7313	Intermediate Similarity	NPD7698	Approved
0.731	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD5689	Approved
0.731	Intermediate Similarity	NPD2200	Suspended
0.731	Intermediate Similarity	NPD5688	Approved
0.7308	Intermediate Similarity	NPD5402	Approved
0.7299	Intermediate Similarity	NPD1243	Approved
0.7295	Intermediate Similarity	NPD7930	Approved
0.7293	Intermediate Similarity	NPD6279	Approved
0.7293	Intermediate Similarity	NPD6280	Approved
0.7288	Intermediate Similarity	NPD2533	Approved
0.7288	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD2534	Approved
0.7288	Intermediate Similarity	NPD5401	Approved
0.7288	Intermediate Similarity	NPD2532	Approved
0.7287	Intermediate Similarity	NPD3818	Discontinued
0.7277	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD5953	Discontinued
0.7263	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7258	Intermediate Similarity	NPD6232	Discontinued
0.7257	Intermediate Similarity	NPD7466	Approved
0.7251	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD6780	Approved
0.725	Intermediate Similarity	NPD6777	Approved
0.725	Intermediate Similarity	NPD6781	Approved
0.725	Intermediate Similarity	NPD6776	Approved
0.725	Intermediate Similarity	NPD6782	Approved
0.725	Intermediate Similarity	NPD6778	Approved
0.725	Intermediate Similarity	NPD6779	Approved
0.7249	Intermediate Similarity	NPD7286	Phase 2
0.7247	Intermediate Similarity	NPD1512	Approved
0.7238	Intermediate Similarity	NPD6386	Approved
0.7238	Intermediate Similarity	NPD6385	Approved
0.7238	Intermediate Similarity	NPD4665	Approved
0.7238	Intermediate Similarity	NPD4111	Phase 1
0.7219	Intermediate Similarity	NPD2313	Discontinued
0.7219	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7214	Intermediate Similarity	NPD2493	Approved
0.7214	Intermediate Similarity	NPD2494	Approved
0.72	Intermediate Similarity	NPD2976	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD2800	Approved
0.7192	Intermediate Similarity	NPD4583	Approved
0.7192	Intermediate Similarity	NPD7871	Phase 2
0.7192	Intermediate Similarity	NPD7870	Phase 2
0.7192	Intermediate Similarity	NPD4582	Approved
0.7191	Intermediate Similarity	NPD4662	Approved
0.7191	Intermediate Similarity	NPD4661	Approved
0.7186	Intermediate Similarity	NPD2974	Approved
0.7186	Intermediate Similarity	NPD2973	Approved
0.7186	Intermediate Similarity	NPD2975	Approved
0.7184	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD7874	Approved
0.7183	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD4575	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD8163	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD8162	Phase 2
0.7174	Intermediate Similarity	NPD3882	Suspended
0.717	Intermediate Similarity	NPD7907	Approved
0.7165	Intermediate Similarity	NPD6990	Approved
0.7165	Intermediate Similarity	NPD6989	Approved
0.7164	Intermediate Similarity	NPD4580	Approved
0.7163	Intermediate Similarity	NPD8469	Approved
0.7159	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD4628	Phase 3
0.7157	Intermediate Similarity	NPD7211	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD8313	Approved
0.715	Intermediate Similarity	NPD5676	Approved
0.715	Intermediate Similarity	NPD8312	Approved
0.7143	Intermediate Similarity	NPD4002	Approved
0.7143	Intermediate Similarity	NPD7435	Discontinued
0.7143	Intermediate Similarity	NPD4004	Approved
0.7135	Intermediate Similarity	NPD7837	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD3450	Approved
0.7129	Intermediate Similarity	NPD7566	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD3452	Approved
0.7128	Intermediate Similarity	NPD3863	Clinical (unspecified phase)
0.7127	Intermediate Similarity	NPD3226	Approved
0.7118	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD6874	Approved
0.7097	Intermediate Similarity	NPD6862	Phase 2
0.7093	Intermediate Similarity	NPD5124	Phase 1
0.7093	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD8366	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