NPASS Compound

Natural Product: NPC216802

Natural Product ID	NPC216802
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	CEMJRABGGWOEJQ-WHCXSEIWSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	6325548
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides [CHEMONTID:0001580] Triterpene glycosides [CHEMONTID:0002358] Triterpene saponins

The Chemical Classification was calculated by Classyfire, a software for chemical taxonomy calculation. Reference: DOI:10.1186/s13321-016-0174-y.

Chemical Representations

RDKit 3D 103108 0 0 0 0 0 0 0 0999 V2000 1.3051 -4.2382 -2.4295 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9490 -2.8695 -2.4297 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5197 -2.7232 -3.8664 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9945 -1.7738 -2.1277 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1425 -1.0367 -0.8494 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2282 -0.5482 -0.4399 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6310 0.5784 -0.9605 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9537 1.2586 -0.7009 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5333 0.7594 0.6103 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9130 1.3417 0.8204 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3947 1.3040 2.2468 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8772 2.8454 0.4939 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6510 3.2032 -0.7260 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1033 2.7393 -0.6450 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.2137 1.2840 -0.2705 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1822 1.0052 0.8043 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7941 0.5875 -1.5283 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8348 0.7262 -0.1597 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7850 -0.7746 -0.2439 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4506 -1.4052 -0.1779 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4345 -0.7240 0.7121 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.8083 -1.1496 2.1295 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0728 -1.3058 0.5086 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1544 -2.7826 0.1555 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2048 -1.3603 1.7493 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0543 -2.0969 1.4410 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8588 -1.6680 0.2719 C 0 0 1 0 0 0 0 0 0 0 0 0 2.7189 -2.8589 -0.1371 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1503 -2.8678 -1.5479 C 0 0 2 0 0 0 0 0 0 0 0 0 4.0747 -1.8832 -1.8886 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8764 -0.6946 0.8427 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8596 -0.3199 2.0327 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8874 -0.1710 0.0519 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8499 0.7376 0.5728 C 0 0 1 0 0 0 0 0 0 0 0 0 6.2522 0.1213 0.4842 C 0 0 1 0 0 0 0 0 0 0 0 0 7.1794 0.9656 1.3289 C 0 0 2 0 0 0 0 0 0 0 0 0 7.0970 2.3689 0.8100 C 0 0 1 0 0 0 0 0 0 0 0 0 5.6554 2.8285 0.6495 C 0 0 1 0 0 0 0 0 0 0 0 0 5.6972 4.1948 -0.0003 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2465 4.0775 -1.2713 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8838 1.9380 -0.0908 O 0 0 0 0 0 0 0 0 0 0 0 0 7.6966 3.2016 1.7445 O 0 0 0 0 0 0 0 0 0 0 0 0 8.4982 0.5306 1.1779 O 0 0 0 0 0 0 0 0 0 0 0 0 6.2429 -1.1865 0.9634 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.8510 3.5507 0.2286 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6241 -4.8185 -1.5439 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6467 -4.8488 -3.3019 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2026 -4.1727 -2.5557 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9991 -1.7538 -3.9866 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7069 -2.9159 -4.6002 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2818 -3.5105 -4.0306 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0720 -2.1302 -2.3069 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0723 -1.0766 -3.0304 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7678 -0.1297 -1.1415 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0658 1.0846 -1.6620 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8507 2.3495 -0.7815 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5411 0.9762 -1.5971 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8909 1.2285 1.4036 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5452 1.1704 2.9428 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7464 2.3493 2.5652 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2820 0.7038 2.4389 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8926 3.2842 0.4963 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3991 3.4377 1.3300 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1985 2.9587 -1.6907 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7442 4.3329 -0.7187 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5223 2.9533 -1.6537 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2187 1.1047 0.3462 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2356 1.7849 1.6184 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1537 -0.0205 1.1619 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0429 0.5283 -2.3219 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6575 1.2442 -1.8385 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2116 -0.3924 -1.2710 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4420 1.0286 -1.1883 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3268 -1.1476 -1.1654 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4140 -1.1676 0.5928 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6133 -2.4591 0.2093 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1221 -1.5448 -1.2247 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6431 -2.2661 2.2502 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1707 -0.6973 2.9051 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8982 -1.1017 2.3207 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3970 -3.4127 1.0371 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8915 -3.0474 -0.6075 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1881 -3.1908 -0.1995 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7341 -1.9806 2.5008 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0029 -0.3888 2.1929 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6672 -1.9871 2.4002 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9379 -3.2170 1.4194 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1247 -3.7736 0.0743 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6076 -2.9521 0.5332 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6673 -3.8467 -1.7212 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5141 -2.1804 -2.7294 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6821 0.9482 1.6572 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6221 0.1340 -0.5476 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9163 0.9045 2.4085 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6569 2.3998 -0.1537 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2244 2.8677 1.6706 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4284 4.7987 0.6078 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7196 4.6693 -0.0785 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9622 4.8663 -1.8024 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6682 3.3637 1.5677 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7021 0.2761 0.2363 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3104 -1.1865 1.9490 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3541 3.8601 1.0013 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 2 4 1 0 4 5 1 0 5 6 1 0 6 7 2 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 1 1 10 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 15 17 1 0 15 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 1 21 23 1 0 23 24 1 0 23 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 27 31 1 1 31 32 2 0 31 33 1 0 33 34 1 0 34 35 1 0 35 36 1 0 36 37 1 0 37 38 1 0 38 39 1 0 39 40 1 0 38 41 1 0 37 42 1 0 36 43 1 0 35 44 1 0 14 45 1 0 29 2 1 0 41 34 1 0 27 5 1 0 23 6 1 0 21 9 1 0 18 10 1 0 1 46 1 0 1 47 1 0 1 48 1 0 3 49 1 0 3 50 1 0 3 51 1 0 4 52 1 0 4 53 1 0 5 54 1 0 7 55 1 0 8 56 1 0 8 57 1 0 9 58 1 0 11 59 1 0 11 60 1 0 11 61 1 0 12 62 1 0 12 63 1 0 13 64 1 0 13 65 1 0 14 66 1 6 16 67 1 0 16 68 1 0 16 69 1 0 17 70 1 0 17 71 1 0 17 72 1 0 18 73 1 0 19 74 1 0 19 75 1 0 20 76 1 0 20 77 1 0 22 78 1 0 22 79 1 0 22 80 1 0 24 81 1 0 24 82 1 0 24 83 1 0 25 84 1 0 25 85 1 0 26 86 1 0 26 87 1 0 28 88 1 0 28 89 1 0 29 90 1 1 30 91 1 0 34 92 1 1 35 93 1 6 36 94 1 1 37 95 1 6 38 96 1 1 39 97 1 0 39 98 1 0 40 99 1 0 42100 1 0 43101 1 0 44102 1 0 45103 1 0 M END

Standard InCHIKey	CEMJRABGGWOEJQ-WHCXSEIWSA-N
Standard InCHI	InChI=1S/C36H58O9/c1-31(2)16-20-19-8-9-23-33(5)12-11-24(38)32(3,4)22(33)10-13-35(23,7)34(19,6)14-15-36(20,17-25(31)39)30(43)45-29-28(42)27(41)26(40)21(18-37)44-29/h8,20-29,37-42H,9-18H2,1-7H3/t20?,21-,22?,23?,24+,25+,26-,27+,28-,29+,33+,34?,35-,36-/m1/s1
SMILES	CC1(C)CC2C3=CCC4[C@@]5(C)CC[C@@H](C(C)(C)C5CC[C@@]4(C)C3(C)CC[C@]2(C[C@@H]1O)C(=O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	634.41	Volume:	653.712 ? Van der Waals volume.
Dense:	0.97	LogP:	3.062 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.461 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.077 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	4.0	Rigid Bonds:	33.0
TPSA:	156.91 ? Topological Polar Surface Area.	H-Bond Acceptor:	9.0
H-Bond Donor:	6.0	Rings:	6.0
Heavy Atoms:	9.0

MedChem Properties

QED Drug-Likeness Score:	0.202	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.392	Fsp³:	0.917
MCE-18:	130.783 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.842	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.012 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.016 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.153	Promiscuous compounds:	0.038

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.873	MDCK Permeability:	-5.105
Pgp-inhibitor:	0.0	Pgp-substrate:	0.719
PAMPA:	1.0 ? The experimental data for Peff was logarithmically transformed (logPeff). Molecules with log Peff values below 2.0 were classified as low-permeability (Category 0), while those with log Peff values exceeding 2.5 were classified as high-permeability (Category 1).	Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.548	30% Bioavailability (F30%):	0.704
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.503	MRP1:	0.755
Plasma Protein Binding (PPB):	81.209%	Volume Distribution (VD):	-0.115
Fu:	11.804% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.022
BSEP inhibitor:	0.004

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.955	CYP2C19-substrate:	0.011
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.04
CYP3A4-inhibitor:	0.703	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.106
HLM stability:	0.054 ? Human liver microsomal (HLM) stability. Category 0: stable+ (HLM > 30 min); Category 1: unstable- (HLM ≤ 30 min). The output value is the probability of human liver microsomal instability, where a value closer to 1 indicates a higher likelihood of instability.

ADMET: Excretion

Clearance (CL):

2.31

Half-life (T1/2):

2.541

ADMET: Toxicity

hERG Blockers:	0.009	hERG Blockers (10um):	0.03
Human Hepatotoxicity (H-HT):	0.707	Drug-induced Liver Injury (DILI):	0.08
AMES Toxicity:	0.439	Rat Oral Acute Toxicity:	0.055
Maximum Recommended Daily Dose:	0.555	Skin Sensitization:	0.999
Carcinogencity:	0.499	Eye Corrosion:	0.0
Eye Irritation:	0.002	Respiratory Toxicity:	0.074
Drug-induced Neurotoxicity:	0.001	Ototoxicity:	0.989
Hematotoxicity:	0.087	Drug-induced Nephrotoxicity:	0.55
Genotoxicity:	0.433	RPMI-8226 Immunitoxicity:	0.057
A549 Cytotoxicity:	0.87	Hek293 Cytotoxicity:	0.493
BCF:	1.639 ? Bioconcentration factors are used for considering secondary poisoning potential and assessing risks to human health via the food chain. The unit is -log10[(mg/L)/(1000*MW)].	IGC50:	4.269 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.882 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.066 ? 96 hour fathead minnow LC50. The unit of LC50FM is -log10[(mg/L)/(1000*MW)].

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO1551	Luffa aegyptiaca	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1551	Luffa aegyptiaca	Species	Cucurbitaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO1551	Luffa aegyptiaca	Species	Cucurbitaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO1551	Luffa aegyptiaca	Species	Cucurbitaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO1551	Luffa aegyptiaca	Species	Cucurbitaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO1551	Luffa aegyptiaca	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1551	Luffa aegyptiaca	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO1551	Luffa aegyptiaca	Species	Cucurbitaceae	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	Organism Name	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

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

Experimental ADME

Experiment Model	Experiment Tissue	ADME Type	ADME Relation	ADME Value	ADME Unit	Reference

Experimental Toxicity

Quantitative toxicity

Experiment Model	Experiment Organism	Toxicity Type	Toxicity Relation	Toxicity Value	Toxicity Unit	Reference

Common Abbreviations:
LC: Lethal Concentration; LD: Lethal Dose; LT:Lethal Time; NOAEL: No-observed-adverse-effect Level; BMDL: Benchmark Dose Lower Confidence Limit; BMD: Benchmark Dose; BMC:Benchmark Concentration; LOAEL: Lowest Observed Adverse Effect Level; RfD:Reference Dose; RfC:Reference Concentration; MRL: Minimal Risk Level; MEG: Maximum Exposure Guideline; PAC: Protective Action Criteria

Categorical toxicity labels

Hepatotoxicity	Carcinogenicity	Mutagenicity	Cardiotoxicity	Respiratory Toxicity	Eye Irritation	Endocrine Disruption

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 toxicity records from domain-specific databases. These databases include:
☉ ToxValDB: a curated database that compiles quantitative toxicity values for chemicals from diverse public sources to support toxicological research and risk assessment.
☉ TOXRIC: a comprehensive, free-to-access, online database providing toxicological/feature data. The toxicity labels are retrieved from this database. [PMID: 36400569]

Chemically structural similarity

Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes approximately 50,000 NPs with experimentally-derived bioactivity available in NPASS)

Similarity is measured using the Tanimoto coefficient (Tc) , which compares the binary fingerprints of two molecules. Tc is calculated as the intersection divided by the union of '1' bits in the fingerprints, ranging from 0 to 1, with 1 indicating highest similarity.

● The left chart: Distribution of similarity level between NPC216802 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	20587
0.1-0.2	23119
0.2-0.3	4585
0.3-0.4	1128
0.4-0.5	304
0.5-0.6	92
0.6-0.7	31
0.7-0.8	0
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8514	High Similarity	NPC167383
0.8	Intermediate Similarity	NPC191763
0.7595	Intermediate Similarity	NPC237503
0.7468	Intermediate Similarity	NPC46388
0.6829	Remote Similarity	NPC605954
0.6818	Remote Similarity	NPC29069
0.6786	Remote Similarity	NPC68419
0.6667	Remote Similarity	NPC37739
0.6667	Remote Similarity	NPC306746
0.6588	Remote Similarity	NPC137917
0.6395	Remote Similarity	NPC7870
0.6395	Remote Similarity	NPC310014
0.6395	Remote Similarity	NPC269315
0.6395	Remote Similarity	NPC75747
0.6353	Remote Similarity	NPC116794
0.6333	Remote Similarity	NPC90856
0.6333	Remote Similarity	NPC214484
0.6292	Remote Similarity	NPC209894
0.625	Remote Similarity	NPC104071
0.6196	Remote Similarity	NPC48499
0.6136	Remote Similarity	NPC110139
0.6136	Remote Similarity	NPC108709
0.6105	Remote Similarity	NPC39211
0.6092	Remote Similarity	NPC199457
0.6064	Remote Similarity	NPC235405
0.6064	Remote Similarity	NPC139894
0.6064	Remote Similarity	NPC475516
0.6053	Remote Similarity	NPC246708
0.602	Remote Similarity	NPC473459
0.6	Remote Similarity	NPC473373
0.6	Remote Similarity	NPC249848
0.6	Remote Similarity	NPC150400
0.6	Remote Similarity	NPC128925
0.6	Remote Similarity	NPC107966
0.6	Remote Similarity	NPC256798
0.5955	Remote Similarity	NPC271138
0.5955	Remote Similarity	NPC102914
0.5938	Remote Similarity	NPC295371
0.5938	Remote Similarity	NPC473884
0.5938	Remote Similarity	NPC157868
0.5889	Remote Similarity	NPC220984
0.5876	Remote Similarity	NPC473343
0.5876	Remote Similarity	NPC469946
0.5843	Remote Similarity	NPC604133
0.5816	Remote Similarity	NPC192791
0.5816	Remote Similarity	NPC223301
0.5816	Remote Similarity	NPC242840
0.5816	Remote Similarity	NPC171544
0.5816	Remote Similarity	NPC112352
0.58	Remote Similarity	NPC235438
0.5758	Remote Similarity	NPC30735
0.5758	Remote Similarity	NPC309714
0.5743	Remote Similarity	NPC222580
0.57	Remote Similarity	NPC40775
0.57	Remote Similarity	NPC10607
0.57	Remote Similarity	NPC251768
0.57	Remote Similarity	NPC159309
0.57	Remote Similarity	NPC102439
0.57	Remote Similarity	NPC46665
0.57	Remote Similarity	NPC480475
0.57	Remote Similarity	NPC86222
0.5699	Remote Similarity	NPC47063
0.5684	Remote Similarity	NPC179434
0.5644	Remote Similarity	NPC475591
0.5644	Remote Similarity	NPC63159
0.5644	Remote Similarity	NPC236870
0.5638	Remote Similarity	NPC204458
0.5638	Remote Similarity	NPC189884
0.5638	Remote Similarity	NPC269095
0.5638	Remote Similarity	NPC138334
0.5631	Remote Similarity	NPC104372
0.5618	Remote Similarity	NPC190837
0.56	Remote Similarity	NPC109588
0.5588	Remote Similarity	NPC297263
0.5579	Remote Similarity	NPC78046
0.5556	Remote Similarity	NPC475171
0.5545	Remote Similarity	NPC11551
0.5524	Remote Similarity	NPC80986
0.5495	Remote Similarity	NPC48249
0.5488	Remote Similarity	NPC49776
0.5488	Remote Similarity	NPC63118
0.5488	Remote Similarity	NPC474436
0.5481	Remote Similarity	NPC281148
0.5481	Remote Similarity	NPC114484
0.5472	Remote Similarity	NPC31838
0.5437	Remote Similarity	NPC31193
0.5429	Remote Similarity	NPC301449
0.5429	Remote Similarity	NPC601290
0.5417	Remote Similarity	NPC1046
0.54	Remote Similarity	NPC161674
0.5392	Remote Similarity	NPC305267
0.5385	Remote Similarity	NPC65590
0.5385	Remote Similarity	NPC125923
0.5377	Remote Similarity	NPC481030
0.5377	Remote Similarity	NPC480473
0.5377	Remote Similarity	NPC480474
0.5361	Remote Similarity	NPC475208
0.5354	Remote Similarity	NPC58448
0.5347	Remote Similarity	NPC75417
0.5327	Remote Similarity	NPC481078
0.5327	Remote Similarity	NPC187290
0.5325	Remote Similarity	NPC101475
0.5288	Remote Similarity	NPC609763
0.5283	Remote Similarity	NPC481079
0.5263	Remote Similarity	NPC607754
0.5256	Remote Similarity	NPC235341
0.525	Remote Similarity	NPC40552
0.5234	Remote Similarity	NPC96641
0.5234	Remote Similarity	NPC163183
0.5225	Remote Similarity	NPC481031
0.5192	Remote Similarity	NPC148417
0.519	Remote Similarity	NPC159168
0.5161	Remote Similarity	NPC187056
0.5161	Remote Similarity	NPC606216
0.5161	Remote Similarity	NPC607023
0.5146	Remote Similarity	NPC160415
0.5135	Remote Similarity	NPC79643
0.5132	Remote Similarity	NPC290598
0.5132	Remote Similarity	NPC30590
0.5119	Remote Similarity	NPC164349
0.5096	Remote Similarity	NPC101744
0.5093	Remote Similarity	NPC69811
0.506	Remote Similarity	NPC488519
0.5054	Remote Similarity	NPC479080
0.5048	Remote Similarity	NPC68175
0.5044	Remote Similarity	NPC135904
0.5044	Remote Similarity	NPC123199

Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC216802 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7344
0.1-0.2	1723
0.2-0.3	78
0.3-0.4	4
0.4-0.5	1
0.5-0.6	0
0.6-0.7	0
0.7-0.8	0
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
		NPD

Bioactivity similarity

Similar Natural Products in NPASS

Similarity level is defined by 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