NPASS Compound

Structure

NPC472291 OpenBabel07101718202D 27 31 0 0 1 0 0 0 0 0999 V2000 -0.4487 -1.6747 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6747 2.2437 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3381 -3.1412 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8994 0.7074 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1685 0.1556 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2870 0.7502 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8252 -0.3533 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0288 0.6875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1450 -0.8433 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8975 0.8975 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4487 -0.7772 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.9437 0.2413 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3358 0.1558 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6747 -0.4487 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2128 -0.3105 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4519 0.8975 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.7589 -0.8433 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4519 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2292 -0.4487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5609 -1.7949 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8975 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.7712 -0.7369 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.6747 1.3462 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.0658 -1.6867 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.3381 -1.3462 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5609 -2.6924 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 11 1 0 0 0 0 2 23 1 0 0 0 0 3 26 1 0 0 0 0 4 5 2 0 0 0 0 4 6 1 0 0 0 0 5 7 1 0 0 0 0 6 12 2 0 0 0 0 7 15 2 0 0 0 0 8 13 1 0 0 0 0 9 14 1 0 0 0 0 9 17 1 0 0 0 0 10 23 1 0 0 0 0 11 21 1 1 0 0 0 11 27 1 0 0 0 0 12 13 1 0 0 0 0 12 15 1 0 0 0 0 13 19 2 0 0 0 0 14 18 1 0 0 0 0 14 21 1 1 0 0 0 15 22 1 0 0 0 0 16 8 1 6 0 0 0 16 18 1 0 0 0 0 16 23 1 0 0 0 0 17 19 1 0 0 0 0 17 24 2 0 0 0 0 18 20 1 6 0 0 0 19 22 1 0 0 0 0 20 25 2 0 0 0 0 20 26 1 0 0 0 0 21 10 1 6 0 0 0 21 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	368.17
Volume:	370.326
LogP:	2.551
LogD:	2.391
LogS:	-3.971
# Rotatable Bonds:	2
TPSA:	74.93
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.617
Synthetic Accessibility Score:	5.393
Fsp3:	0.524
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.991
MDCK Permeability:	3.2221149012912065e-05
Pgp-inhibitor:	0.146
Pgp-substrate:	0.024
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.01
30% Bioavailability (F30%):	0.24

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.965
Plasma Protein Binding (PPB):	50.017417907714844%
Volume Distribution (VD):	1.571
Pgp-substrate:	57.578433990478516%

ADMET: Metabolism

CYP1A2-inhibitor:	0.689
CYP1A2-substrate:	0.929
CYP2C19-inhibitor:	0.059
CYP2C19-substrate:	0.895
CYP2C9-inhibitor:	0.026
CYP2C9-substrate:	0.097
CYP2D6-inhibitor:	0.292
CYP2D6-substrate:	0.875
CYP3A4-inhibitor:	0.63
CYP3A4-substrate:	0.744

ADMET: Excretion

Clearance (CL):	14.988
Half-life (T1/2):	0.115

ADMET: Toxicity

hERG Blockers:	0.11
Human Hepatotoxicity (H-HT):	0.159
Drug-inuced Liver Injury (DILI):	0.281
AMES Toxicity:	0.189
Rat Oral Acute Toxicity:	0.953
Maximum Recommended Daily Dose:	0.892
Skin Sensitization:	0.604
Carcinogencity:	0.712
Eye Corrosion:	0.022
Eye Irritation:	0.014
Respiratory Toxicity:	0.989

Download Data

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

Natural Product: NPC472291

Natural Product ID:	NPC472291
*Common Name:**	BRWYCRLKASLULK-IRZFUUSHSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	BRWYCRLKASLULK-IRZFUUSHSA-N
Standard InCHI:	InChI=1S/C21H24N2O4/c1-11-21(27-11)10-23(2)16-8-13-12-6-4-5-7-15(12)22-19(13)17(24)9-14(21)18(16)20(25)26-3/h4-7,11,14,16,18,22H,8-10H2,1-3H3/t11-,14-,16-,18-,21-/m0/s1
SMILES:	CC1C2(O1)CN(C3CC4=C(C(=O)CC2C3C(=O)OC)NC5=CC=CC=C45)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3358044
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0002744] Vobasan alkaloids

*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
NPO32666	tabernaemontana	Genus	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25333996]

☑ 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	3

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	=	5.7	ug.mL-1	PMID[494252]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	25.0	ug.mL-1	PMID[494252]

☑ 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 NPC472291 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	313
0.1-0.2	1644
0.2-0.3	8727
0.3-0.4	20474
0.4-0.5	6757
0.5-0.6	2590
0.6-0.7	1911
0.7-0.8	265
0.8-0.85	10
0.85-0.9	5
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9048	High Similarity	NPC247735
0.9048	High Similarity	NPC81802
0.9048	High Similarity	NPC269886
0.9048	High Similarity	NPC472210
0.9048	High Similarity	NPC472295
0.8698	High Similarity	NPC472292
0.866	High Similarity	NPC472293
0.8622	High Similarity	NPC472297
0.8622	High Similarity	NPC472296
0.8177	Intermediate Similarity	NPC469896
0.8119	Intermediate Similarity	NPC254240
0.8119	Intermediate Similarity	NPC214428
0.8119	Intermediate Similarity	NPC199851
0.8119	Intermediate Similarity	NPC312870
0.8119	Intermediate Similarity	NPC128265
0.8119	Intermediate Similarity	NPC294909
0.8098	Intermediate Similarity	NPC277350
0.795	Intermediate Similarity	NPC472113
0.794	Intermediate Similarity	NPC472112
0.7921	Intermediate Similarity	NPC472116
0.7871	Intermediate Similarity	NPC220151
0.7871	Intermediate Similarity	NPC19692
0.7846	Intermediate Similarity	NPC219336
0.7804	Intermediate Similarity	NPC312645
0.78	Intermediate Similarity	NPC196251
0.78	Intermediate Similarity	NPC63199
0.78	Intermediate Similarity	NPC102338
0.78	Intermediate Similarity	NPC111602
0.7795	Intermediate Similarity	NPC183662
0.7795	Intermediate Similarity	NPC15573
0.7795	Intermediate Similarity	NPC217372
0.7793	Intermediate Similarity	NPC477979
0.7793	Intermediate Similarity	NPC70155
0.7783	Intermediate Similarity	NPC475778
0.7778	Intermediate Similarity	NPC162730
0.7773	Intermediate Similarity	NPC234999
0.7772	Intermediate Similarity	NPC55493
0.7761	Intermediate Similarity	NPC314333
0.7761	Intermediate Similarity	NPC329858
0.7752	Intermediate Similarity	NPC475271
0.7746	Intermediate Similarity	NPC229348
0.7745	Intermediate Similarity	NPC245916
0.7711	Intermediate Similarity	NPC175474
0.7703	Intermediate Similarity	NPC132539
0.7692	Intermediate Similarity	NPC474116
0.7692	Intermediate Similarity	NPC33949
0.7688	Intermediate Similarity	NPC472119
0.7685	Intermediate Similarity	NPC281049
0.767	Intermediate Similarity	NPC52557
0.7664	Intermediate Similarity	NPC89508
0.7662	Intermediate Similarity	NPC472323
0.7656	Intermediate Similarity	NPC165599
0.7642	Intermediate Similarity	NPC469743
0.7638	Intermediate Similarity	NPC143533
0.7635	Intermediate Similarity	NPC472097
0.763	Intermediate Similarity	NPC244741
0.7617	Intermediate Similarity	NPC118940
0.7614	Intermediate Similarity	NPC14113
0.7614	Intermediate Similarity	NPC145885
0.7614	Intermediate Similarity	NPC84827
0.7608	Intermediate Similarity	NPC476874
0.7596	Intermediate Similarity	NPC49196
0.7596	Intermediate Similarity	NPC313985
0.7596	Intermediate Similarity	NPC79129
0.7596	Intermediate Similarity	NPC195461
0.7596	Intermediate Similarity	NPC81654
0.7596	Intermediate Similarity	NPC249150
0.7591	Intermediate Similarity	NPC64216
0.7591	Intermediate Similarity	NPC266192
0.7581	Intermediate Similarity	NPC221100
0.7581	Intermediate Similarity	NPC234078
0.7569	Intermediate Similarity	NPC52254
0.7548	Intermediate Similarity	NPC241024
0.7525	Intermediate Similarity	NPC66210
0.7525	Intermediate Similarity	NPC235684
0.7523	Intermediate Similarity	NPC267926
0.7523	Intermediate Similarity	NPC82070
0.7512	Intermediate Similarity	NPC258480
0.7512	Intermediate Similarity	NPC476114
0.75	Intermediate Similarity	NPC50503
0.7489	Intermediate Similarity	NPC57453
0.7488	Intermediate Similarity	NPC79356
0.7488	Intermediate Similarity	NPC102592
0.7477	Intermediate Similarity	NPC21638
0.7475	Intermediate Similarity	NPC472107
0.7475	Intermediate Similarity	NPC79062
0.7463	Intermediate Similarity	NPC139291
0.7463	Intermediate Similarity	NPC472108
0.7452	Intermediate Similarity	NPC141454
0.745	Intermediate Similarity	NPC15840
0.7442	Intermediate Similarity	NPC123839
0.7437	Intermediate Similarity	NPC234987
0.7431	Intermediate Similarity	NPC36405
0.7416	Intermediate Similarity	NPC149708
0.74	Intermediate Similarity	NPC283219
0.74	Intermediate Similarity	NPC248041
0.74	Intermediate Similarity	NPC126709
0.7397	Intermediate Similarity	NPC249428
0.7395	Intermediate Similarity	NPC478158
0.7385	Intermediate Similarity	NPC313640
0.7376	Intermediate Similarity	NPC159125
0.7364	Intermediate Similarity	NPC174788
0.7357	Intermediate Similarity	NPC474192
0.7357	Intermediate Similarity	NPC475720
0.7356	Intermediate Similarity	NPC57994
0.7356	Intermediate Similarity	NPC289299
0.7349	Intermediate Similarity	NPC266249
0.7333	Intermediate Similarity	NPC21174
0.7333	Intermediate Similarity	NPC478078
0.7333	Intermediate Similarity	NPC271797
0.7333	Intermediate Similarity	NPC57690
0.7317	Intermediate Similarity	NPC14994
0.7316	Intermediate Similarity	NPC475816
0.7304	Intermediate Similarity	NPC133003
0.7302	Intermediate Similarity	NPC477065
0.73	Intermediate Similarity	NPC267885
0.7291	Intermediate Similarity	NPC472104
0.729	Intermediate Similarity	NPC475847
0.729	Intermediate Similarity	NPC185742
0.7289	Intermediate Similarity	NPC472762
0.7273	Intermediate Similarity	NPC148183
0.7273	Intermediate Similarity	NPC152768
0.7273	Intermediate Similarity	NPC474121
0.7268	Intermediate Similarity	NPC160381
0.7268	Intermediate Similarity	NPC478077
0.726	Intermediate Similarity	NPC54744
0.7256	Intermediate Similarity	NPC238457
0.725	Intermediate Similarity	NPC203468
0.725	Intermediate Similarity	NPC149155
0.725	Intermediate Similarity	NPC110500
0.7249	Intermediate Similarity	NPC473105
0.7246	Intermediate Similarity	NPC324091
0.7243	Intermediate Similarity	NPC476098
0.7243	Intermediate Similarity	NPC476115
0.7241	Intermediate Similarity	NPC113626
0.7241	Intermediate Similarity	NPC71037
0.724	Intermediate Similarity	NPC472285
0.7237	Intermediate Similarity	NPC290529
0.7227	Intermediate Similarity	NPC478157
0.7227	Intermediate Similarity	NPC474412
0.7225	Intermediate Similarity	NPC267343
0.7222	Intermediate Similarity	NPC474905
0.7214	Intermediate Similarity	NPC151635
0.7212	Intermediate Similarity	NPC25401
0.7208	Intermediate Similarity	NPC115232
0.7206	Intermediate Similarity	NPC472109
0.7206	Intermediate Similarity	NPC472110
0.72	Intermediate Similarity	NPC191310
0.7198	Intermediate Similarity	NPC221873
0.7195	Intermediate Similarity	NPC469928
0.7192	Intermediate Similarity	NPC91179
0.7185	Intermediate Similarity	NPC473800
0.7177	Intermediate Similarity	NPC67551
0.7174	Intermediate Similarity	NPC284888
0.7169	Intermediate Similarity	NPC82370
0.7164	Intermediate Similarity	NPC189812
0.7164	Intermediate Similarity	NPC329688
0.7163	Intermediate Similarity	NPC469470
0.7163	Intermediate Similarity	NPC469501
0.715	Intermediate Similarity	NPC471944
0.7149	Intermediate Similarity	NPC194740
0.7149	Intermediate Similarity	NPC311906
0.7149	Intermediate Similarity	NPC471303
0.7143	Intermediate Similarity	NPC472099
0.7143	Intermediate Similarity	NPC182222
0.7143	Intermediate Similarity	NPC55772
0.7137	Intermediate Similarity	NPC148889
0.7136	Intermediate Similarity	NPC318299
0.7136	Intermediate Similarity	NPC74413
0.7136	Intermediate Similarity	NPC293917
0.713	Intermediate Similarity	NPC54803
0.713	Intermediate Similarity	NPC321592
0.713	Intermediate Similarity	NPC96321
0.7129	Intermediate Similarity	NPC84347
0.7124	Intermediate Similarity	NPC229893
0.7122	Intermediate Similarity	NPC159963
0.7119	Intermediate Similarity	NPC191489
0.7117	Intermediate Similarity	NPC330009
0.7116	Intermediate Similarity	NPC193761
0.7116	Intermediate Similarity	NPC260900
0.7115	Intermediate Similarity	NPC321708
0.7114	Intermediate Similarity	NPC161861
0.7114	Intermediate Similarity	NPC472123
0.7104	Intermediate Similarity	NPC317752
0.7101	Intermediate Similarity	NPC62749
0.7101	Intermediate Similarity	NPC315555
0.7097	Intermediate Similarity	NPC18661
0.7094	Intermediate Similarity	NPC111275
0.7089	Intermediate Similarity	NPC67288
0.7087	Intermediate Similarity	NPC474688
0.7081	Intermediate Similarity	NPC154339
0.7078	Intermediate Similarity	NPC472070
0.7073	Intermediate Similarity	NPC88923
0.7073	Intermediate Similarity	NPC315634
0.7073	Intermediate Similarity	NPC100734
0.7073	Intermediate Similarity	NPC191415
0.7064	Intermediate Similarity	NPC270918
0.7061	Intermediate Similarity	NPC24370
0.7061	Intermediate Similarity	NPC319232
0.7056	Intermediate Similarity	NPC123395

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 NPC472291 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	183
0.1-0.2	527
0.2-0.3	727
0.3-0.4	2022
0.4-0.5	2941
0.5-0.6	2150
0.6-0.7	546
0.7-0.8	52
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8119	Intermediate Similarity	NPD4501	Approved
0.8119	Intermediate Similarity	NPD4500	Approved
0.7897	Intermediate Similarity	NPD6770	Approved
0.7761	Intermediate Similarity	NPD4499	Approved
0.7725	Intermediate Similarity	NPD4506	Discontinued
0.7596	Intermediate Similarity	NPD4600	Approved
0.7596	Intermediate Similarity	NPD4601	Approved
0.7593	Intermediate Similarity	NPD3393	Approved
0.7593	Intermediate Similarity	NPD3394	Approved
0.7593	Intermediate Similarity	NPD3389	Approved
0.7571	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.755	Intermediate Similarity	NPD2095	Phase 2
0.755	Intermediate Similarity	NPD2094	Phase 2
0.755	Intermediate Similarity	NPD2092	Phase 2
0.7535	Intermediate Similarity	NPD6657	Clinical (unspecified phase)
0.7512	Intermediate Similarity	NPD2510	Approved
0.7512	Intermediate Similarity	NPD2509	Approved
0.7512	Intermediate Similarity	NPD2096	Phase 2
0.7512	Intermediate Similarity	NPD2091	Phase 2
0.7436	Intermediate Similarity	NPD5482	Discontinued
0.7406	Intermediate Similarity	NPD6176	Phase 1
0.7381	Intermediate Similarity	NPD6661	Clinical (unspecified phase)
0.7376	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD5003	Discontinued
0.7356	Intermediate Similarity	NPD4602	Approved
0.7339	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD4736	Clinical (unspecified phase)
0.7316	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD2214	Approved
0.7268	Intermediate Similarity	NPD2213	Approved
0.725	Intermediate Similarity	NPD482	Approved
0.7237	Intermediate Similarity	NPD8372	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD7727	Phase 2
0.7214	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD8114	Approved
0.7209	Intermediate Similarity	NPD8115	Approved
0.7202	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD5721	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD3006	Discontinued
0.717	Intermediate Similarity	NPD4987	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD2565	Phase 2
0.7163	Intermediate Similarity	NPD2564	Approved
0.7162	Intermediate Similarity	NPD8325	Phase 3
0.7162	Intermediate Similarity	NPD8327	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD8326	Phase 3
0.715	Intermediate Similarity	NPD7817	Phase 1
0.7143	Intermediate Similarity	NPD5450	Discontinued
0.7136	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD5632	Approved
0.7119	Intermediate Similarity	NPD7708	Approved
0.7114	Intermediate Similarity	NPD750	Phase 2
0.7108	Intermediate Similarity	NPD5473	Discontinued
0.7097	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD1630	Approved
0.7091	Intermediate Similarity	NPD7470	Discontinued
0.7087	Intermediate Similarity	NPD7688	Phase 1
0.7083	Intermediate Similarity	NPD8072	Approved
0.7073	Intermediate Similarity	NPD7803	Approved
0.7059	Intermediate Similarity	NPD7454	Approved
0.7059	Intermediate Similarity	NPD7455	Approved
0.7054	Intermediate Similarity	NPD6578	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD7878	Phase 2
0.7051	Intermediate Similarity	NPD5901	Discontinued
0.7051	Intermediate Similarity	NPD8098	Approved
0.7051	Intermediate Similarity	NPD3947	Discontinued
0.705	Intermediate Similarity	NPD2844	Phase 3
0.7043	Intermediate Similarity	NPD4952	Phase 3
0.7037	Intermediate Similarity	NPD8073	Approved
0.7031	Intermediate Similarity	NPD6292	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD7958	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD7957	Phase 1
0.7015	Intermediate Similarity	NPD1573	Approved
0.7015	Intermediate Similarity	NPD1575	Approved
0.7005	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7004	Intermediate Similarity	NPD6160	Clinical (unspecified phase)
0.6996	Remote Similarity	NPD8112	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD1631	Approved
0.6983	Remote Similarity	NPD6263	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD8096	Phase 3
0.6982	Remote Similarity	NPD8097	Phase 3
0.6967	Remote Similarity	NPD6630	Clinical (unspecified phase)
0.6953	Remote Similarity	NPD4373	Phase 2
0.695	Remote Similarity	NPD2915	Discontinued
0.6948	Remote Similarity	NPD4427	Phase 2
0.6942	Remote Similarity	NPD5897	Approved
0.6942	Remote Similarity	NPD5898	Approved
0.6942	Remote Similarity	NPD5899	Approved
0.6941	Remote Similarity	NPD7001	Phase 3
0.6937	Remote Similarity	NPD7070	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD5475	Discontinued
0.693	Remote Similarity	NPD53	Approved
0.693	Remote Similarity	NPD7777	Approved
0.693	Remote Similarity	NPD7778	Approved
0.6923	Remote Similarity	NPD4520	Approved
0.6916	Remote Similarity	NPD1996	Discontinued
0.6905	Remote Similarity	NPD4948	Discontinued
0.6895	Remote Similarity	NPD5426	Phase 3
0.6887	Remote Similarity	NPD5912	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD5913	Phase 3
0.6878	Remote Similarity	NPD5104	Approved
0.6875	Remote Similarity	NPD5596	Phase 2
0.687	Remote Similarity	NPD7955	Approved
0.687	Remote Similarity	NPD7956	Approved
0.6861	Remote Similarity	NPD8013	Clinical (unspecified phase)
0.6858	Remote Similarity	NPD8406	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD2920	Discontinued
0.6847	Remote Similarity	NPD4184	Clinical (unspecified phase)
0.6844	Remote Similarity	NPD3757	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD7818	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD7903	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD4174	Clinical (unspecified phase)
0.683	Remote Similarity	NPD7594	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD1586	Approved
0.6822	Remote Similarity	NPD5891	Approved
0.6818	Remote Similarity	NPD2721	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD7809	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD8160	Phase 2
0.681	Remote Similarity	NPD7994	Phase 2
0.6802	Remote Similarity	NPD7947	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD8248	Clinical (unspecified phase)
0.6787	Remote Similarity	NPD2715	Clinical (unspecified phase)
0.6777	Remote Similarity	NPD4426	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD6665	Discontinued
0.6774	Remote Similarity	NPD4397	Phase 1
0.6752	Remote Similarity	NPD5479	Discontinued
0.6751	Remote Similarity	NPD7853	Phase 2
0.6746	Remote Similarity	NPD3178	Discontinued
0.6743	Remote Similarity	NPD6249	Phase 2
0.6743	Remote Similarity	NPD6248	Phase 2
0.6742	Remote Similarity	NPD8272	Phase 2
0.6742	Remote Similarity	NPD6987	Phase 1
0.6738	Remote Similarity	NPD7731	Approved
0.6738	Remote Similarity	NPD7730	Approved
0.6737	Remote Similarity	NPD7789	Approved
0.6737	Remote Similarity	NPD7953	Approved
0.6737	Remote Similarity	NPD7950	Approved
0.6737	Remote Similarity	NPD7951	Approved
0.6737	Remote Similarity	NPD7790	Approved
0.6737	Remote Similarity	NPD7791	Approved
0.6737	Remote Similarity	NPD7952	Approved
0.6731	Remote Similarity	NPD1587	Approved
0.673	Remote Similarity	NPD5075	Discontinued
0.6729	Remote Similarity	NPD5592	Clinical (unspecified phase)
0.6729	Remote Similarity	NPD2336	Approved
0.6726	Remote Similarity	NPD8423	Phase 2
0.6726	Remote Similarity	NPD8399	Phase 1
0.6724	Remote Similarity	NPD7271	Approved
0.6714	Remote Similarity	NPD3318	Approved
0.6714	Remote Similarity	NPD3319	Phase 1
0.6714	Remote Similarity	NPD4334	Discontinued
0.6714	Remote Similarity	NPD7234	Approved
0.6714	Remote Similarity	NPD1534	Approved
0.6714	Remote Similarity	NPD3320	Approved
0.6714	Remote Similarity	NPD7233	Approved
0.6712	Remote Similarity	NPD484	Approved
0.6712	Remote Similarity	NPD6479	Discontinued
0.6712	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD6183	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD43	Approved
0.6699	Remote Similarity	NPD4524	Discontinued
0.6699	Remote Similarity	NPD6182	Approved
0.6698	Remote Similarity	NPD5809	Phase 3
0.6696	Remote Similarity	NPD7970	Approved
0.6696	Remote Similarity	NPD5293	Phase 2
0.6696	Remote Similarity	NPD7941	Phase 3
0.6696	Remote Similarity	NPD7971	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD8289	Discontinued
0.6683	Remote Similarity	NPD2144	Approved
0.6682	Remote Similarity	NPD3436	Approved
0.6681	Remote Similarity	NPD7824	Approved
0.668	Remote Similarity	NPD6716	Phase 1
0.6667	Remote Similarity	NPD7825	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8283	Approved
0.6667	Remote Similarity	NPD3038	Discontinued
0.6667	Remote Similarity	NPD56	Approved
0.6667	Remote Similarity	NPD8282	Approved
0.6667	Remote Similarity	NPD4643	Clinical (unspecified phase)
0.6652	Remote Similarity	NPD3243	Approved
0.664	Remote Similarity	NPD8463	Approved
0.6639	Remote Similarity	NPD8358	Approved
0.6638	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6638	Remote Similarity	NPD6995	Phase 1
0.6637	Remote Similarity	NPD7289	Clinical (unspecified phase)
0.6637	Remote Similarity	NPD4901	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD7944	Discontinued
0.6624	Remote Similarity	NPD4885	Approved
0.6623	Remote Similarity	NPD6242	Discontinued
0.6623	Remote Similarity	NPD5417	Clinical (unspecified phase)
0.6622	Remote Similarity	NPD6529	Discontinued
0.662	Remote Similarity	NPD5444	Phase 1
0.6619	Remote Similarity	NPD8464	Clinical (unspecified phase)
0.6619	Remote Similarity	NPD1643	Phase 3
0.6617	Remote Similarity	NPD4326	Phase 2
0.661	Remote Similarity	NPD8374	Phase 3
0.6609	Remote Similarity	NPD6173	Approved
0.6609	Remote Similarity	NPD7547	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD8493	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD8322	Phase 2
0.6606	Remote Similarity	NPD2307	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